This is Michael Seibel with Dalton Caldwell. Today we're going to talk about how overthinking is sometimes a founder's biggest mistake. Dalton, this video was triggered by an amazing meme you made about fundraising advice. Before we get to the meme — because I think it's one of the best I've ever seen on fundraising — let's start in general: how can overthinking be bad, and when can it be bad?

I think that what people imagine being a founder is comes from watching the Facebook movie or popular television, where you're coding all the time and making deals and screwing over your friends — just kidding. In reality, it's a lot of feeling lost, not being sure what to do, feeling stressed out, and worrying all the time, so you tend to overthink everything and every decision. You think in circles over and over because you don't have a boss or clear constraints when you're a startup founder — there's no one really telling you what to do, so you're on your own. And so the experience of being a startup founder is to always be overthinking everything.

In this way, there's a bit of advantage to being young, right?

Yeah, you and I experienced this ourselves as founders where we were young when we first started and this is the beauty of not knowing anything. The beauty of not knowing anything is that you think everything is easy and none of the innumerable reasons why something might be hard or your startup might fail even occurs to you. You're like, oh yeah, I'm 22, everything's easy, I can figure this out. And so again, this is like the midwit meme where if you don't know anything, your approach looks a lot like the approach of people that are really good founders. And the worst place to be is that you know just enough to know why the things you're trying are hard and the odds are stacked against you. And that freaks you out. And so you think about it a lot, right?

So Dalton, one of the most perfect examples of this is actually Elon Musk and why I think it's so perfect is that depending on how you tell the story, Elon looks like the dummy or the genius, right? Depending on how you tell the story and it almost doesn't matter, right? Cause he's winning. But you know, to me, the first example that I always loved is that, you know, I read some book about the starting of SpaceX and it started with Elon going to Russia, trying to buy like rockets. And like the Russian government being like, there's this American billionaire guy who wants to buy rockets and kind of not believing it, but Elon just looking really serious. So they like considered it. And like they eventually said, no, but like, he got to talk to people about buying rockets from them. He's just a dude with money.

He was like, go to Russia, buy rockets. Like that's the extreme. Is that genius or stupid? I can't tell.

I can't tell.

And with Tesla itself, to me the midwit meme is "electric cars are good" — that's the extreme. In the middle it's, "No one has successfully done a startup car company since the 50s, and if you look at all prior attempts to build an electric car, there are all these reasons it's hard, even though electric cars are good."

Yes. And I think the one that we find most funny — and we'll see if this video can stand the test of time — is the Boring Company, right? Drilling holes under the ground so that you can drive places faster is very clearly the "idiot" one, but it could be the "genius" one too.

It's exact, it's a beginner's mind idea, which is like traffic is bad. What if we dug a hole under the ground to get to downtown Las Vegas? And what's funny is you read all the critiques of this, like the Midwestern, it's like, well, bus systems already exist. And it's much more efficient to optimize transportation. There's lots of words in the middle of that. But drill tunnel to avoid traffic is certainly at the extremes. And you kind of see him approach all of his problems this way, where you can imagine it being the same sort of ideas that we, Mars is cool. Yeah, Mars is cool. This is the kind of stuff we come up with as teenagers. A lot of ideas.

Yes. And the hard work is in the implementation, but the idea isn't very complicated. And the V1 is kind of simple-minded.

And if he were an overthinker, he would rule all this stuff out. All of it is obviously a bad idea. Anyone in the midwit territory would rule out all these ideas.

Yes. And they still do. They still do. It's the Tesla short seller, right?

Let's go through some examples of the Midwit meme. And you have to start with the meme that you made for YC founders. So just to provide context, we're in the part of the batch where YC founders start getting nervous about fundraising. Whenever a founder gets nervous, they start overthinking. And whenever they start overthinking, they assault us with office hours on topics and Dalton created this meme so that we could fight back. What does the meme say?

This comes up a lot with MVPs. One of the questions that I love getting from a founder is before we launched our MVP, how do we know we're going to be able to survive the onslaught of traffic and users that will come on our launch day? What's the midwit play? What's the midwit meme for your MVP?

Yeah, the two extremes of the Midwit meme are launch something fast. Build something fast and put it out. And the Midwit one is like, well, I don't want to get a bad reputation that my thing was buggy and we only have one shot to launch. And you know, like...

What about the press? We have to do a press launch; it doesn't have to be an event.

Yeah, I don't want people to see my idea and copy it. So it's got to be perfect.

And then do we do a TechCrunch post, or is it better to try to get the New York Times? What about Hacker News? We need to get all three, so how do we coordinate them?

We want to we want to be featured in the New York Times. And so how do we optimize for that? Or Oh, what should we name the company?

Yes. We have to rebrand because there's a name that's kind of similar to ours. We don't want people to be confused.

How about co-founders? I hear this a lot like I am a business person and I'm good at sales. I need to find a marketing co-founder and an engineer like a CTO who's already managed 50 people because we're going to grow fast. But how does co-founders, how do you see this thing go?

It's like. Yeah, Dalton. I'm open to the idea of a co-founder. I just haven't found the right person. And what I really am looking for, someone with at least five to seven years of experience at Google, who made it to at least a L7. And so, you know, I haven't found the right person yet, but we're looking for it.

Yes. When we find them, I'm totally open to bring out a co-founder when I find that one.

But first we're going to raise money, and then I think that'll attract a better co-founder. So again, the point we're kind of making is not that any one of these ideas is the one people say it's that It's thinking in circles and having a thousand different reasons that the person that should be your co-founder is no one that you currently know.

And then let's talk about the other sides of the equation, right? On the dumb side, the founder's like, it's fun to work with my friends. So I'm just going to start working with my friend, right?

Justin Kan likes to put a camera on his head. You're like, this is our guy.

We were drinking buddies.

Why didn't they pick you? Is their co-founder was like?

Well, because I helped them find an apartment and open up a bank account.

There you go. Boom. This guy helped us find an apartment. All right. He's the co-founder of Twitch. Done.

There you go. Done.

And then the super smart experienced founders, like, oh, having a co-founder is viable for emotional support. And I know this is going to be tricky. And they have all the sophisticated reasons. Same answer. Same answer. I love that.

Okay. Next, this is a classic one, especially because you have to deal with so many admissions questions. Applying to YC, Dalton, what is the Jedi founder move to apply to YC versus the midwit founder?

Yeah. The extremes of this and the midwit meme are, "I filled out my application and submitted it. I applied." And the midwit founder is like, "Gee, I don't know if now is the right time to apply. I don't know if we're ready. I'm going to write a draft of my application and send it to 15 people, and I'm going to get feedback on my application. I need an introduction to alumni and I need to talk to alumni."

And I need recommendations. Yeah, recommendations from strangers that don't know me.

I'm going to do a lot of research. You talk to people who put months of effort into their application to YC — strategy that is not correlated with success — and then you talk to people and they're like, "Oh yeah, I just filled it out in 30 minutes."

And I spent all that other time working on my company.

We're not saying do a bad job on your application. We're just saying that trying to tweak it endlessly is something you can spend tons and tons of time on, and I'm not sure that's a great allocation of resources.

No. And I think that's like maybe the essential point here is that like, we want you to spend time on the important stuff for your startup. Like we're trying to get you to avoid spending time on the things that won't help you. That's the idea. That's the idea.

All right. Next, and here's kind of a classic one is product market fit. Dalton, do I have product market fit? And how, what's the midwit approach to product?

The midwit approach for this one is to be unsure if you have it and create 15 different metrics and a complicated series of thoughts that maybe you have it or you have early product market fit. The extremes on this meme are, "Am I overwhelmed with demand?" You know it when you see it. You don't have to think very hard when you have it — it sort of hits you over the head when you have product market fit.

I think the extremes in the meme is like, did I sleep last night? It's like, I didn't sleep last night. Something must be going well.

Do I have time to wonder if I have product market fit? If you have time to wonder about it, if you're like, gee, do I have product market fit? Let me, let's pontificate on this. That probably means you don't.

Yes. Let's do some, let's make some reports. So, we talk about all the situations where maybe overthinking is not a good idea. But you also describe, you know, there are certain six situations, you call them trapdoor decisions when maybe you want to think a little bit harder than before making a move. So what are some examples of those?

Yeah, so, legal issues. Don't break any laws. Saying you didn't know there was a law is not a great legal defense. Regulatory issues are similar — "Oh, I didn't know that I couldn't launder this money" — probably not great. You may want to overthink that and look into it. For things that affect people's health and well-being, you should overthink that. You should really spend the time worrying about people.

Let's not be fast and loose when we're building an online pharmacy. Let's measure twice and cut once. And I think that what really good founders do is they are very good at figuring out whether they are dealing with something like that or not. Because even within legal, there are certain things that are like, "Oh, this is whatever," and certain things that are really bad.

Michael, should I file patents for all of my IP?

Exactly.

That's a classic overthinking. Probably not.

So I think that like, The framework here is really twofold. One, don't overthink when you don't have to. And then two, remember that most of the work is not in these overthinking games. Like most of the work are not in these over-optimizing games.

Yeah, it's action. Taking action and not thinking, right?

Yes, yes. It's launching. It's getting the first customer. It's selling. It's like it's doing these things yourself. And that's kind of intuitive because I think that founders understand that startups are really hard. So they assume you need complex strategies to succeed. And it's like, ah, that's a hard thing. It makes sense when I say it, right? If this is hard, we would need a complex strategy, right? How do you respond to that? It's like, what actual kind of strategy do you need?

I think if you haven't seen really successful startup companies either personally — where you were the founder of one — or you know people and you saw them go through it, it's hard to believe how silly these things are when they start. Unless you've literally witnessed it personally and you've seen the silly shit that goes on and what it really takes to get big, your brain rejects the idea that that's actually how these companies got built. You're like, "No, not true. It had to be lots of strategy meetings and whiteboarding, flow charts, and Gartner magic quadrants." Your brain won't allow you to see that. Actually, here's a nice way to say it: you know the term "beginner's mind." You want to have a beginner's mind. That's what the midwit meme is. And a beginner's mind is, "I guess I'm going to build a product and I'm going to give it to people. I guess I'm going to deliver burritos." That's a beginner's mind approach.

That's the game. And so you might find yourself after watching this video asking yourself, what do I need to unlearn?

Yeah, how can I have a beginner's mind? Because again, this is the beauty of the midwit meme is the genius and the idiot come to the same conclusion. So what is the idiot approach? Like, that's actually how you can divine the genius approach. You're like, what would an idiot do?

Everyone can reach for the idiot approach. Everyone has the intellectual capacity to reach for the idiot approach.

Yeah, If I didn't know anything...

So with all that being said, Have fun and don't overthink it too much. Don't overthink it too much and make sure that you have a little bit of something in your head that's asking yourself, is this the thing that's really important? If not, I can move on.