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Y CombinatorThe Student's Guide To Becoming A Successful Startup Founder
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EVERY SPOKEN WORD
25 min read · 5,190 words- 0:00 – 1:12
Intro
- DCDalton Caldwell
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.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
That's, that's the point.
- MSMichael Seibel
That's the point. That's why the world needs young people. [laughs] This is Michael Seibel with Dalton Caldwell, and today we're gonna talk about our advice for high schoolers.
- DCDalton Caldwell
Uh-oh.
- MSMichael Seibel
It's been a little while.
- DCDalton Caldwell
[laughs]
- MSMichael Seibel
It's been a little while. [laughs] So maybe the place to start, 'cause I think that, um, oftentimes young people are in a rush, maybe we can just start by saying the startup game isn't going away.
- DCDalton Caldwell
That's true.
- MSMichael Seibel
You've got time.
- DCDalton Caldwell
And look, I think to set this up, we know a lot of young people watch these videos.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
We know they like startup content. We know they, um, may even anonymously be involved in startups on Discord and stuff.
- MSMichael Seibel
Sure, sure, sure.
- DCDalton Caldwell
Like, it, it's crazy, for the folks that apply to YC, a lot of them are, are-
- MSMichael Seibel
Yep
- DCDalton Caldwell
... literally in high school.
- MSMichael Seibel
Yep.
- DCDalton Caldwell
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.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
But we wanna speak directly to you high school students who are-
- MSMichael Seibel
Yes, yes
- DCDalton Caldwell
... who are trying to figure out, who are ambitious and wanna be a part of what's happening in the tech world, in the, you know, startup world-
- MSMichael Seibel
Yep
- DCDalton Caldwell
... and aren't really sure where to begin.
- MSMichael Seibel
Yes.
- 1:12 – 2:23
Delayed Gratification
- MSMichael Seibel
Maybe the first analogy I give you, and, and this will immediately age me, so I apologize. I was a big Final Fantasy VII player. You play Fin- FF VII?
- DCDalton Caldwell
A little bit.
- MSMichael Seibel
Of course. All right. The basic thing I learned in Final Fantasy VII was that you can fight the boss at a certain level and get your ass kicked.
- DCDalton Caldwell
[laughs]
- MSMichael Seibel
Or you can grind for, like, you know, 10 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 startup world, where, like, investing and leveling yourself up can produce a lot of benefits later on. Like, deferring a little bit of that satisfaction of getting started right now so you can up-skill makes you 10 times more powerful later. But let's be clear, you have to be up-skilling during that time. [laughs]
- DCDalton Caldwell
Yeah, you gotta be grinding.
- MSMichael Seibel
You gotta be grinding.
- DCDalton Caldwell
Like, the grind has to happen.
- MSMichael Seibel
Exactly. [laughs] If I just sit there and didn't grind, my character got no better. [laughs] And what's cool, in a video game you see grinding. It's a lot easier.
- DCDalton Caldwell
Yeah, your le- you can see the character-
- MSMichael Seibel
You can s-
- DCDalton Caldwell
... leveling up.
- MSMichael Seibel
Exactly.
- DCDalton Caldwell
Like, learning new spells or whatever.
- MSMichael Seibel
E- exactly.
- DCDalton Caldwell
Yeah.
- MSMichael Seibel
But, um, in the real world, let's talk a little bit about grinding.
- 2:23 – 4:17
Learn to Code
- MSMichael Seibel
What's the kinda grinding, what's the kind of up-skilling that you would advise high schoolers to do?
- DCDalton Caldwell
Well, the most obvious and straightforward one is learn how to code.
- MSMichael Seibel
Obvious.
- DCDalton Caldwell
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 wanna be a coder my whole life. I wanna be a founder, I wanna be a product person." Well, you should still learn how to code. [laughs] Like, there's, it's really hard to make an argument-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... if you're a young person why you shouldn't have that skill in your skill tree. Can you make a case why you wouldn't?
- MSMichael Seibel
How do you make the case?
- DCDalton Caldwell
[laughs]
- MSMichael Seibel
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 I didn't have the power to impact the product anywhere near as much as my other three co-founders who were, who were software engineers. So, like, this is such an obvious one. [laughs]
- DCDalton Caldwell
Yeah, and you got time.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
Like, this is a great thing.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
AP computer science.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
You can take Replit. Like, there's all these YC companies-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... that help people learn how to code.
- MSMichael Seibel
Code Academy, there's so many. Yes.
- DCDalton Caldwell
So even if you have some complicated relationship with maybe I don't wanna be a programmer, that's fine.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
Learn the skill.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
This is like, it's like learning how to cast spells or something. [laughs]
- MSMichael Seibel
Well, I'll push even harder. Like, get this complicated view of I don't wanna 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 inside the s-
- DCDalton Caldwell
They're the most highly compensated, they're the hardest to replace.
- MSMichael Seibel
They often have the best ideas. They often have the be- the easiest, the easiest path to implementing their ideas, by far. [laughs] Like, they're the power center. The talkers, not as much.
- DCDalton Caldwell
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."
- MSMichael Seibel
Doesn't matter.
- DCDalton Caldwell
I'm just trying to argue you don't need to be that.
- 4:17 – 4:52
Learn Design
- MSMichael Seibel
two, um, we talked about this a little bit. Design. Learning how to use basic design software.
- DCDalton Caldwell
Yeah.
- MSMichael Seibel
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 needed to be made and we didn't have a designer-
- DCDalton Caldwell
It was on you.
- MSMichael Seibel
Yeah. [laughs]
- DCDalton Caldwell
[laughs]
- MSMichael Seibel
Make the button, you know? Like, it didn't even have to look that good. Um, and so this is a skill that anyone can grasp for, and, like, there's examples of good design and bad design-
- DCDalton Caldwell
Yeah
- MSMichael Seibel
... all over the internet, right? So you can easily copy.
- 4:52 – 6:49
Launch Products
- MSMichael Seibel
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, 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.
- DCDalton Caldwell
'Cause you're doing reps.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
Like, one of the things I noticed at YC is a lot of the folks that later on become great founders-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... they worked on projects in high school that may not be commercially, like, venture-funded companies, but they were, like, pretty cool.
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
And so one of the examples I always think of was, um, back in the '90s there was a computer program called Winamp.
- MSMichael Seibel
Yep.
- DCDalton Caldwell
And that's how you would listen to the MP3s you downloaded from Napster.
- MSMichael Seibel
Yep.
- DCDalton Caldwell
And some high school kids, um, Mark Zuckerberg and Adam D'Angelo, I believe, built a music recommendation plugin for Winamp.
- MSMichael Seibel
Yep.
- DCDalton Caldwell
And it was quite popular. I think it was called, like, The Brain or something like that.
- MSMichael Seibel
Something like that, yeah.
- DCDalton Caldwell
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 r- write code, they knew how to make something they themselves wanted, which was music recommendation for Winamp.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
And they released it, and I think it got, like, millions of downloads. It was pretty popular.
- MSMichael Seibel
They went through all the motions a startup founder has to. But in this kind of, like, no stakes-
- DCDalton Caldwell
Yeah
- MSMichael Seibel
... you know?
- DCDalton Caldwell
They weren't trying to-
- MSMichael Seibel
Yeah
- DCDalton Caldwell
... it wasn't a business, at least to my understanding. Maybe, maybe they thought it was, but I, it was more of making something cool.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
And this sort of story comes up a lot in a-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... in our f- some of the founders that we fund, is that they do stuff like this.
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
And you'll ask them, "Well, why, why were you doing that?" And they almost don't understand the question.
- 6:49 – 8:04
Make Friends
- DCDalton Caldwell
young.
- MSMichael Seibel
The next one that comes up a lot, if you're gonna be a startup founder one day, you gotta learn how to talk to people. Gotta learn how to make friends.
- DCDalton Caldwell
Yep.
- MSMichael Seibel
And needless to say, I think that this is a skill that people kind of assume you can't learn. Like, assume like, oh, some people are just really social-
- DCDalton Caldwell
Yeah
- MSMichael Seibel
... 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-
- DCDalton Caldwell
Absolutely
- MSMichael Seibel
... massively change [laughs] you know? Like-
- DCDalton Caldwell
Absolutely
- MSMichael Seibel
... this is 100% a learnable skill, and anyone who says otherwise is really doing you a, a disservice.
- DCDalton Caldwell
Yep.
- MSMichael Seibel
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.
- DCDalton Caldwell
Yeah. And you have to be willing to be uncomfortable. Again, I-
- MSMichael Seibel
S-
- DCDalton Caldwell
... I think my high school mentality, I don't know if you felt the same way, is you believe too much that your identity then-
- MSMichael Seibel
[laughs]
- DCDalton Caldwell
... like, that's a nerd, that's a jock, that's a th-
- MSMichael Seibel
[laughs]
- DCDalton Caldwell
Like, it was like you would put people in, sort people into buckets-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... like they were, like, permanent.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
And that's fake.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
That shit is not permanent. Everyone could be anything-
- MSMichael Seibel
Yes, yes
- DCDalton Caldwell
... [laughs] if they choose to.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
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.
- MSMichael Seibel
Totally do that.
- 8:04 – 9:13
School Sandbox
- MSMichael Seibel
Well, and it's 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?
- DCDalton Caldwell
Not a ton.
- MSMichael Seibel
Not a ton, right?
- DCDalton Caldwell
Not a ton.
- MSMichael Seibel
So like, one, that reputation's not gonna follow you in the real world, and two, you can experiment. Like, you, you can play. Like-
- DCDalton Caldwell
You can be whoever you wanna be. [laughs]
- MSMichael Seibel
Yeah. If you make a fool of yourself, you go to college, you're not gonna see those people ever again. [laughs]
- DCDalton Caldwell
[laughs]
- MSMichael Seibel
Like, it's totally fine. Totally fine. And I think that, um, 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-
- DCDalton Caldwell
Yeah
- MSMichael Seibel
... of them, being a little bit like, "Oh, I'm-"
- DCDalton Caldwell
And I think when you're older, you get that.
- MSMichael Seibel
Yes. You get it, okay.
- DCDalton Caldwell
But man, you don't get that, you don't get that the popular kids are like-
- MSMichael Seibel
No
- DCDalton Caldwell
... have their own thing they're working on-
- MSMichael Seibel
Exactly
- DCDalton Caldwell
... that they're struggling with.
- MSMichael Seibel
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. [laughs]
- 9:13 – 11:20
Learn To Care
- MSMichael Seibel
I think another one here is, like, how to help people. I think that, um, 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, a- 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-
- DCDalton Caldwell
[laughs]
- MSMichael Seibel
... on the, like, National Merit Scholarship, whatever the, the, the contest of the thing. And I remember, you know, I was maybe 11th grade, and I was tutoring this 9th 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.
- DCDalton Caldwell
[laughs]
- MSMichael Seibel
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 it. Like, if you actually help them, right? If you care. And I actually took it more seriously. Um, and it was funny 'cause 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." [laughs] They were like, "Just come back next week. It's totally fine." [laughs] And I think you might find that with your customers. Like, even if you screw up, like, if you really care and you're really helping them, they're not gonna fire you. [laughs]
- DCDalton Caldwell
[laughs]
- MSMichael Seibel
They're not gonna fire you. It's, it is so rare to find products or people who actually care.
- DCDalton Caldwell
Yeah.
- MSMichael Seibel
It, that's a rare thing.
- DCDalton Caldwell
Especially from young people. Again, like, people are really impressed when young people care.
- MSMichael Seibel
Give a shit. [laughs]
- DCDalton Caldwell
[laughs] It's, you like, like, teachers notice, like, people notice.
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
I don't know. It's, it's a way to stand out. Um-
- MSMichael Seibel
Yeah. [laughs] It's a very easy way to stand out.
- 11:20 – 13:35
Credential Game
- MSMichael Seibel
Um, 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.
- DCDalton Caldwell
Yep.
- MSMichael Seibel
But we don't live in that world.
- DCDalton Caldwell
Don't.
- MSMichael Seibel
Right? So how, how would you tell a high schooler to think about this game?
- DCDalton Caldwell
There's the people that, like, love the system and embrace the system.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
Like the teacher's pets.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
And then there's the people that see the system for what it is-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... and they wanna rage against the machine and destroy the system.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
And you know, I was a little bit more on that side.
- MSMichael Seibel
God, yes.
- DCDalton Caldwell
You know, um-
- MSMichael Seibel
The Stanford kid. Yeah, exactly. [laughs]
- DCDalton Caldwell
No, but, but the key thing is, I, I'm telling you, I'm talking high school, pre-start. I'm just trying to say, like, when you see the system-
- MSMichael Seibel
You got into Stanford [laughs]
- DCDalton Caldwell
... and you see how the world works-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... you're like, "Man, this is, like, not ideal."
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
I think is one way to say it.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
Um-
- MSMichael Seibel
A little fucked up.
- DCDalton Caldwell
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-
- MSMichael Seibel
Yeah
- DCDalton Caldwell
... I think that's much better than, like, rejecting the system out of hand.
- 13:35 – 15:42
Fads That Stick
- MSMichael Seibel
All right. Let's talk about fads.
- DCDalton Caldwell
Yeah.
- MSMichael Seibel
There've been a lot of fads. [laughs]
- DCDalton Caldwell
Yeah. Well, I think it's easy, especially when you're young, to just cau- get caught up in stuff, whatever the thing is.
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
And some of the things are pretty cool. Again, I was really into the internet. [laughs]
- MSMichael Seibel
Yep, yep, yep.
- DCDalton Caldwell
When that was a new thing.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
I was really, really, really into it.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
And obviously, that stuck around.
- MSMichael Seibel
Yep.
- DCDalton Caldwell
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 WallStreetBets and Reddit.
- MSMichael Seibel
Yeah, yeah.
- DCDalton Caldwell
Like, you'll see people get really into stuff.
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
And so it's actually great fun, uh, uh, in, in the Zuckerberg case-
- MSMichael Seibel
Yeah
- DCDalton Caldwell
... building, uh, Winamp plugins, that was part of the Napster thing.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
So they were really into that.
- MSMichael Seibel
Yeah, yeah.
- DCDalton Caldwell
But how... You know, where could it go f- too far, Michael? Uh...
- MSMichael Seibel
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 kinda 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.
- DCDalton Caldwell
That's a great point.
- MSMichael Seibel
Um, on the flip side, we see the opposite of this in the startup world all the time, where, like, COVID happens, everyone wants to have a Zoom startup, and it's like-
- DCDalton Caldwell
Yes. [laughs]
- MSMichael Seibel
The Zoom guys thought people needed video conferencing-
- DCDalton Caldwell
[laughs]
- 15:42 – 17:50
Be Excited
- MSMichael Seibel
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, um, everyone thought technology was cool and making the world a better place.
- DCDalton Caldwell
Yeah. A lot of the way we understand the world is framed via journalism.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
And one thing, again, for young people, they don't have context on this.
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
But it used to be journalists were all emphatically excited with no downsides-
- MSMichael Seibel
No reservations
- DCDalton Caldwell
... no reservations.
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
The internet is great.
- MSMichael Seibel
Yes. [laughs] It's made the world a better place.
- DCDalton Caldwell
And they would debate how great it was.
- MSMichael Seibel
Yeah. [laughs]
- DCDalton Caldwell
[laughs] The debate was like-
- MSMichael Seibel
Yeah. [laughs]
- DCDalton Caldwell
... "Yeah, yeah, we know it's great, but just how great?"
- MSMichael Seibel
Yeah. And who's making it the be-
- DCDalton Caldwell
[laughs]
- MSMichael Seibel
Who's making it the better the fastest, you know? Yeah.
- DCDalton Caldwell
And so it was this... It was hard to, like, see any problems with it.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
And, um, in this current universe we live in-
- MSMichael Seibel
It's the opposite
- DCDalton Caldwell
... yeah, it's this is bad, a lot of these people are bad.
- MSMichael Seibel
Every new technology, how is it gonna try to screw us, exploit us?
- DCDalton Caldwell
Yeah.
- MSMichael Seibel
You know, yada, yada, yada. And let's be clear, both extremes are incorrect.
- DCDalton Caldwell
That's correct.
- MSMichael Seibel
[laughs]
- DCDalton Caldwell
Yeah. No, those are fair points.
- 17:50 – 20:08
Be Honest
- MSMichael Seibel
Let's talk about honesty.
- DCDalton Caldwell
Yep.
- MSMichael Seibel
This is a big one. This is a big one that I think people, um, 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, um, they get caught. So how do you think about learning to be honest if you're a high schooler?
- DCDalton Caldwell
The best skill is to learn to be honest to yourself. [laughs]
- MSMichael Seibel
Yeah. Yeah.
- DCDalton Caldwell
Like, if you, if your own relationship with yourself-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... is you can't be honest about things. What do you really feel? What do you really think? Who are you really?
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
It's gonna be rough.
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
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-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... it's gonna be tricky. And we-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... we, we run across folks that seem like they've deferred a lot of this honesty.
- MSMichael Seibel
Yeah. I think that, um, 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 co-founder might work with you, employee might work with you, um, a lot of reasons why people make things happen in the startup world is because we're in a high-trust environment.
- DCDalton Caldwell
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-
- MSMichael Seibel
Yeah. [laughs] You're supposed to lie all the time. [laughs]
- DCDalton Caldwell
Something, something a nerd would do is be like, "Hey, um, my s- our, that product sucks."
- MSMichael Seibel
Yeah. [laughs]
- DCDalton Caldwell
Like, like, why are we shipping this product that no one wants?
- MSMichael Seibel
Yeah. [laughs]
- DCDalton Caldwell
Like, it's like, "Hey, shut up, man."
- MSMichael Seibel
[laughs]
- DCDalton Caldwell
Like, like, that's like what a, that's what a nerd would do.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
You know, you're bad for telling the truth about something 'cause it's impolite and you're hurting people's feelings.
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
And so there is part of the nerd culture in this that I think is good, which is-
- 20:08 – 23:46
Love The Long Games
- MSMichael Seibel
And then I think the last one is, um, learn to love long games. And this is kind of the theme that we brought up in the beginning. These games are long. And I remember when I started my startup, I was 23 years old, and I'd never done anything that took very long. Like, 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 startup takes seven to 10 years to exit or IPO or sell." And I just thought that couldn't be the case. Like-
- DCDalton Caldwell
[laughs]
- MSMichael Seibel
And, and what's funny is, like, he worked at a law firm, like, he worked at a law firm that represented, like, maybe a quarter of all tech companies. He had the data. [laughs] 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.
- DCDalton Caldwell
[laughs]
- MSMichael Seibel
I was his age when he told me that. I was 30. He was 37, impossibly old. I just remember thinking, "Fuck, the guy was right." Like-
- DCDalton Caldwell
Yeah
- MSMichael Seibel
... this is a long game.
- DCDalton Caldwell
And I think having ambition in your life involves playing the long game.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
Because to actually do something great-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... it doesn't happen overnight.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
And I don't know what your experience is, but we, we've known a lot of people when they were very young.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
And it's okay to have ambition. It's good to have ambition.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
And true ambition means being patient over many, many, many years.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
And so to give you a completely non-startup example, my high school girlfriend-
- MSMichael Seibel
Yep
- DCDalton Caldwell
... her thing was poetry.
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
And she really liked poetry. Again, this is, like, high school.
- MSMichael Seibel
Yeah, yeah, yeah.
- DCDalton Caldwell
And so she'd, like, write all this poetry. She'd read... You know, that was, like, her thing.
- MSMichael Seibel
Yep.
- DCDalton Caldwell
And, you know, I kinda fell out of touch with her, but she's the, um, New York Times poetry critic now.
- MSMichael Seibel
Holy shit. [laughs]
- DCDalton Caldwell
[laughs] And that was my high school girlfriend who loved poetry.
- 23:46 – 24:21
Live Your Dream
- MSMichael Seibel
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.
- DCDalton Caldwell
Hey, don't let it, never let anyone put you down.
- MSMichael Seibel
Yeah, no.
- DCDalton Caldwell
Like, have a dream. We're telling you.
- MSMichael Seibel
It's cool.
- DCDalton Caldwell
Be cool. Be yourself.
- MSMichael Seibel
It's like a-
- DCDalton Caldwell
If that's your dream, we love it.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
Live your dream.
- MSMichael Seibel
Live your dream. The game will be here when you're ready to play, and, you know, we'll be here to help. [upbeat music] All right, man. Great chat. Thank you.
Episode duration: 24:21
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Transcript of episode O5KCB2p6SB8