Dalton + MichaelWant to Build a Great Startup? Start Having Fun.
EVERY SPOKEN WORD
20 min read · 3,520 words- 0:00 – 1:53
Introduction to type two fun
- MSMichael Seibel
Maybe the secret for people who made it this far in the video is the founders who've done great things that you admire, and maybe you admire their strategy, you admire their tactics, what they built, this is probably one of their hidden advantages that you don't see. And especially for the founders who stick with it for, like, a decade, two decades, this is really one of their secret advantages that anyone can grab. This is Dalton + Michael, and today we're gonna talk about something that we like to refer to as type two fun. Dalton, w- what is type two fun?
- DCDalton Caldwell
Yeah, let's start with definitions. We're gonna be talking about hard work today.
- MSMichael Seibel
Mm.
- DCDalton Caldwell
And so-
- MSMichael Seibel
For all you startup founders-
- DCDalton Caldwell
[laughs]
- MSMichael Seibel
... you, you, you should leave, 'cause, like-
- DCDalton Caldwell
It's hard work
- MSMichael Seibel
... startups are hard work. [laughs]
- DCDalton Caldwell
Um, and so look, let's start with type one fun. Type one fun is something that is fun-
- MSMichael Seibel
Yeah
- DCDalton Caldwell
... while you're doing it.
- MSMichael Seibel
Like ice cream.
- DCDalton Caldwell
Ice cream is fun.
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
That's type one fun.
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
Um, type two fun is things that are not fun while you are doing them, but in retrospect you're like, "Oh, that was actually pretty fun."
- MSMichael Seibel
Going to the gym.
- DCDalton Caldwell
[laughs]
- MSMichael Seibel
[laughs]
- DCDalton Caldwell
Climbing a mountain. Any kind of, like, intense-
- MSMichael Seibel
Yeah
- DCDalton Caldwell
... thing that you've done. I think a lot of people, when you look back at the hardest things that you've ever done in your life, like, uh, college or, or what have you-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... in the moment, you're like, "Man, this is hard."
- MSMichael Seibel
Yes.
- DCDalton Caldwell
And then you look back at it wistfully and you wish you were there, because it was super fun in retrospect.
- MSMichael Seibel
Type two fun is often way more rewarding. Like, in my mind, rewarding is the feeling. Versus type one fun feels a little... It's great, but it feels a little empty calories. [laughs]
- DCDalton Caldwell
And so, you know, you and I used to give a talk at the start of every YC batch-
- 1:53 – 4:34
Learning to enjoy hard things
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
And here's, like, the big insight I wanna share, and kind of the theme of the video. You can practice/learn to enjoy doing hard things. [laughs] And you will look back at the, at this time of being a startup founder or, or working as an employee at a startup-
- MSMichael Seibel
Yeah
- DCDalton Caldwell
... that was really, really hard-
- MSMichael Seibel
Yeah
- DCDalton Caldwell
... and realize it was the most fun thing you have ever done in your entire life.
- MSMichael Seibel
[laughs] So I completely agree, and, and I think about this in two ways. One, anyone who's doing a startup or anyone who's talented working in a startup, there's something that you got good at that's really hard, right? And so you've experienced working hard at something, getting good at it, and feeling rewarded, and feeling like that was enjoyable. And a lot of what we're trying to do is put that mental model into the actual practice of building your startup.
- DCDalton Caldwell
Yep.
- MSMichael Seibel
Like, let's try to get you to be as excited about building your startup as you are about engineering or talking to customers. Um, but I think the second thing that I think a lot about is this is, like, the biggest unlock for endurance. We talk a lot about how building a startup takes time. How much time are you going to spend on your startup if every day feels like suffering? And how much time are you gonna spend on your startup if every day feels rewarding? And it's kind of like if you can make that shift, "Oh, man, doing hard work is rewarding. That day was a hard day, but it was fun," you're gonna outlast all your competitors.
- DCDalton Caldwell
[laughs]
- MSMichael Seibel
Right? And what's the YC saying? Like, "If you don't die, you win." So, no, that's kinda how I think about it. The other thing that's interesting is when you hear people talk about their startups in hindsight, what do they talk about?
- DCDalton Caldwell
They talk about how much they miss or, like, how fondly they remember doing really hard things. [laughs]
- MSMichael Seibel
[laughs]
- DCDalton Caldwell
And being a part of a really small team.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
And even if it doesn't work out, people look back at these memories-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... as, as precious. Again, I think we're arguing this is a skill that you could learn.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
And that you choose to frame... This was the advice we give to the founders of the batch. You get to choose of, like, whether you tell yourself a story that, "Wow, YC was really hard."
- MSMichael Seibel
Yep.
- DCDalton Caldwell
"And wow, I didn't sleep at all, and I didn't take care of myself, and we were just suffering the whole time."
- MSMichael Seibel
Yep.
- DCDalton Caldwell
Or you could say, "Wow, this is, like, the coolest thing I've ever done." [laughs]
- MSMichael Seibel
Yes, yes, yes.
- DCDalton Caldwell
"This is the most highly leveraged point of my life."
- MSMichael Seibel
Yes, yes.
- DCDalton Caldwell
And even though you're having the same experience day to day of doing hard things, holy cow, do you come out with a different mentality-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... if you choose to have fun.
- 4:34 – 5:41
The mindset shift in startups
- MSMichael Seibel
Well, and I think it's funny. You know, we talk about at YC a little bit, like, the trough of sorrows, like, when the kind of allure of doing a startup has worn off, but you're pre-product market fit, and you're kind of like, "Oh, crap, this isn't working." And to your point, I think that there's a mindset of, like, "Every day my startup's not working is like hell." There's another mindset, which is like, "Hey, I'm picking this complicated lock."
- DCDalton Caldwell
Yeah.
- MSMichael Seibel
"Or I'm, like, untying this complicated knot, and like, if I figure it out, the reward is so cool. This is more fun than the alternatives." Like, what are the alternatives, right?
- DCDalton Caldwell
Yeah.
- MSMichael Seibel
Like-
- DCDalton Caldwell
This is really living.
- MSMichael Seibel
Exactly.
- DCDalton Caldwell
Yeah, yeah, yeah.
- MSMichael Seibel
Like, I'm alive.
- DCDalton Caldwell
Yes, exactly.
- MSMichael Seibel
[laughs]
- DCDalton Caldwell
'Cause, like-
- MSMichael Seibel
Right
- DCDalton Caldwell
... you can always be at Google and be kind of a cog in the machine, kind of inbox outbox, where, like, you have no idea whether you're having an impact.
- MSMichael Seibel
You're ma-
- DCDalton Caldwell
You-
- MSMichael Seibel
You're taking no risks.
- DCDalton Caldwell
Yeah.
- MSMichael Seibel
You're, you're just kinda like-
- DCDalton Caldwell
You're barely making any decisions, right? And in this situation it's like it's your hands on the knot, right? It's your, like, it's, it's your hands on the lock picks. And to me, if you can convince yourself that that, that being empowered is fun, that working on a hard, viable problem and being empowered is probably the most fun.
- 5:41 – 6:53
Learning to love being uncomfortable
- DCDalton Caldwell
I think the way that I would always talk about this in office hours is to learn to love being uncomfortable.
- MSMichael Seibel
[laughs]
- DCDalton Caldwell
And that human beings are naturally, you know, homeostasis, right? We're always-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... seeking comfort.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
And in any situation we're put in, we're like, "Oh, if this is uncomfortable, I wanna be more comfortable." And if you look at the life of-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... like, you know, many jobs-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... it involves being very comfortable.
- MSMichael Seibel
Mm-hmm.
- DCDalton Caldwell
You know, comfortable seats, comfortable desks. Nothing unexpected ever happens. You know, they do your laundry for you at the office. They-
- MSMichael Seibel
That's almost the def-
- DCDalton Caldwell
... cater lunches
- MSMichael Seibel
... that's almost how you know you're a replaceable cog, right? If nothing in your life suck, uh, uncomfortable, you're very easy to replace.
- DCDalton Caldwell
And so I get that a lot of founders deeply are seeking comfort. It makes sense. It's intuitive. But man, if you can learn to embrace being uncomfortable-
- MSMichael Seibel
Yeah
- DCDalton Caldwell
... and find it fun, and seek uncomfortable-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... that's actually how you stretch yourself to do fantastic work. And the number one way to get good at sales, for instance-
- MSMichael Seibel
Yeah
- DCDalton Caldwell
... is to get comfortable just doing a lot of sales and getting-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... having people tell you no a lot, and getting rejected.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
And you learn to kind of love it.
- 6:53 – 8:38
Transferring grit from life to startups
- MSMichael Seibel
Well, and this is the funny bit, is that, like, you don't have to learn this from scratch. There is something else in your life that you've had this experience with, right? And so in my mind, this is just transferring that knowledge you have, that skill that took a long time, maybe that sport that you did, or maybe that academic subject you got good at. It's just transferring that to the, your startup. And when you look at those things, right, like, you know, if you're in sports, going to the gym, going to practice, da, da, da, da. Like, there were a lot of times that you're just, like, kind of grinding.
- DCDalton Caldwell
And think about it. In those experiences, what actually made you better?
- MSMichael Seibel
It's the time grinding.
- DCDalton Caldwell
It's, like, the pain.
- MSMichael Seibel
Yes. [laughs]
- DCDalton Caldwell
It's basically you only get better-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... if you push yourself to failure.
- MSMichael Seibel
Exactly.
- DCDalton Caldwell
If you push yourself to, you know, your body having to react.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
Right? [laughs]
- MSMichael Seibel
Yes. That's where all of the value comes in that moment.
- DCDalton Caldwell
And again, that, and these people aren't suffering, right? Like they-
- MSMichael Seibel
No
- DCDalton Caldwell
... like-
- MSMichael Seibel
No
- DCDalton Caldwell
... they love playing the game. [laughs]
- MSMichael Seibel
It's funny 'cause when I think about, you know, people always ask me stories about Justin TV and Twitch, and, like, the most horrible thing is that people ask me, like, "Well, what happened the day that, like, the company sold and you got this money?" And my memory is, like, not good. But then if you ask me about the five times the company almost died, I feel like I can give you, like, a, a minute-by-minute, like, [laughs] rundown of, like, "This is what was happening. This is why it sucked. This is what we did. We almost died." And far more rewarding. Like far, like those are the memories I cherish, right?
- DCDalton Caldwell
Yeah.
- MSMichael Seibel
Like, the hardest moments are the memories I cherish. Not that, like, making money was bad, but it's just, like, it, it, it turns out that, like, you know, if we go back to the gym, do you remember the warmup set? Or do you remember, like, your PR when you really-
- DCDalton Caldwell
Right
- MSMichael Seibel
... stretched yourself and you didn't think you could do it?
- 8:38 – 11:01
The competitive edge of type two fun
- MSMichael Seibel
You know? And so I think that the interesting thing for founders to understand is that unfortunately, when there are groups of people, and those groups of people are running away from hard work, you can start thinking that maybe that's the right thing. Like, oh, maybe-
- DCDalton Caldwell
Well-
- MSMichael Seibel
... I'll work hard and let me figure out the hack. Let me-
- DCDalton Caldwell
The-
- MSMichael Seibel
... figure out the cheat.
- DCDalton Caldwell
Why did we give this talk at the beginning of the batch?
- MSMichael Seibel
Yes.
- DCDalton Caldwell
We gave this talk because too many people thought, "I got into YC."
- MSMichael Seibel
Hard work's done.
- DCDalton Caldwell
"Now I can be comfortable. I've done it."
- MSMichael Seibel
[laughs]
- DCDalton Caldwell
"Like, we made it," right? Like, "Oh, I'm on easy street."
- MSMichael Seibel
[laughs]
- DCDalton Caldwell
"What, you know, I got into YC." And we're like, "Hey, folks. Bad news."
- MSMichael Seibel
Ooh. [laughs]
- DCDalton Caldwell
"We, we have some tough news to tell you."
- MSMichael Seibel
Oh. [laughs] Boo.
- DCDalton Caldwell
Like, if that's your mentality, you are not gonna make it.
- MSMichael Seibel
No. [laughs]
- DCDalton Caldwell
And instead, we invite you to learn to embrace doing really uncomfortable things and do it in an environment with peers.
- MSMichael Seibel
Yes. Well, and it's so funny. I think we also want you to embrace being in an uncomfortable environment. Being in an environment where almost everyone is gonna lose is uncomfortable.
- DCDalton Caldwell
Yeah.
- MSMichael Seibel
Right? Like, being motivated in that kind of environment is a superpower. And I remember, you know, we used to say this, PG came up with this, which was basically like the opening of YC, only a small number of you are gonna win. And it's so interesting because when you talk to the folks who ended up winning, they all told the same story. They all were like, "Man, this is depressing, but we're gonna be the one. We're gonna be one of 'em."
- DCDalton Caldwell
[laughs]
- MSMichael Seibel
"Like, we're gonna, we're gonna figure it out." [laughs] And it's like, if you can bring that to the table, I would argue there's so many advantages. You know, if your competition raises more money or has better talent or blah, blah, blah, or they started earlier, and they don't bring this to the table, they don't enjoy type two fun.
- DCDalton Caldwell
Yeah. It, it's almost like, um, you know, plants turn sunlight into energy, you know, photosynthesis.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
Um, great founders turn being uncomfortable into motivation, and in turn, it fuels them.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
They're like, "Yeah." [laughs]
- 11:01 – 12:10
Flipping the mindset switch
- DCDalton Caldwell
time.
- MSMichael Seibel
Well, and the other fun thing I love about that mentality is you're not waiting for the torture to end. And I feel like-
- DCDalton Caldwell
It's 'cause it's not torture. [laughs]
- MSMichael Seibel
Exactly. Whereas I feel like so many founders are like, "So I'm gonna work really hard to my Series B, and then it'll get easy." Or, like, that saying that, like, oh, first you're pushing the rock up the hill, and then you're, like, chasing it down. It's like all of these sayings around, like, now it's gonna be easy, where I don't know about you, but when I talk to, like, the founders of GitCom-
- DCDalton Caldwell
Yeah, it's all not true. Sorry
- MSMichael Seibel
... they're like, yeah, like they're like, that's like the, the, they're getting pummeled by the rock. [laughs]
- DCDalton Caldwell
Yeah.
- MSMichael Seibel
Um, so it's, i- instead of this like, oh, eventually it's gonna be easy, if you get your mindset around I like hard.
- DCDalton Caldwell
That's the key, is I think this is a learnable skill.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
I think if you're watching this video-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... there's, like, a bit in your brain that can flip.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
Where you might be saying to yourself, "Wow, this is really hard, and I'm suffering, and gee, I just can't wait till this milestone happens."
- MSMichael Seibel
Yes.
- DCDalton Caldwell
"I get this number of users."
- MSMichael Seibel
Yes.
- DCDalton Caldwell
"Or I get into YC," or whatever it is. You can just completely change your mentality.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
And it's your choice to be like, "Wow, I'm having an amazing time. Isn't this fun?"
- MSMichael Seibel
Yeah. [laughs]
- DCDalton Caldwell
And I'm alive.
- MSMichael Seibel
Yeah. Yeah. [laughs]
- 12:10 – 13:08
Seeking challenge vs. seeking comfort
- MSMichael Seibel
I wanna, I wanna present a possibly triggering thought, right? So, like, I don't know if you've had this experience, but I had the experience in school of being in some honors classes and some regular classes. And like, in the honors classes, you're around the kids who are grinding, and like they're having fun grinding, and like you're having fun. And in the regular classes, it seems like just showing up is hard work. You would think when you talk to a lot of YC founders or a lot of founders in general that like in that context, the regular class would have been more fun.
- DCDalton Caldwell
Mm-hmm.
- MSMichael Seibel
And it's, it's not.
- DCDalton Caldwell
No.
- MSMichael Seibel
It's absolutely not.
- DCDalton Caldwell
They'd be bored.
- MSMichael Seibel
It-
- DCDalton Caldwell
They're under-stimulated.
- MSMichael Seibel
Exactly.
- DCDalton Caldwell
Right? Like a lot of people-
- MSMichael Seibel
Exactly
- DCDalton Caldwell
... that are well-suited to be founders are under-stimulated doing normal stuff, right?
- MSMichael Seibel
That's why th- that's why they're doing founder.
- DCDalton Caldwell
[laughs]
- MSMichael Seibel
Exactly. And so it's weird. It's this weird thing, which is probably like seeking challenge is probably inherently one of the reasons why you did this, and then seeking comfort is undermining that. Like just seek greater challenge.
- DCDalton Caldwell
Like-
- MSMichael Seibel
And it got you here
- 13:08 – 14:31
Maintaining a healthy foundation
- DCDalton Caldwell
... and like look, this is an important piece of context to give when we would, when we would give this talk.
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
Um, it was to wri- remind people that like they are okay and they can take this risks-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... and to do this little personal inventory.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
And so let's do the little inventory.
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
Do you have enough money to pay the rent?
- MSMichael Seibel
Boom.
- DCDalton Caldwell
Are you personally safe?
- MSMichael Seibel
Yes.
- DCDalton Caldwell
Are you getting sleep?
- MSMichael Seibel
Yes.
- DCDalton Caldwell
Are you eating well?
- MSMichael Seibel
Yes.
- DCDalton Caldwell
Do you have exercise?
- MSMichael Seibel
Yes.
- DCDalton Caldwell
Like basically, we certainly were never like, "Yeah, go, you know, give yourself psychosis and take-
- MSMichael Seibel
No
- DCDalton Caldwell
... incredible risks."
- MSMichael Seibel
No.
- DCDalton Caldwell
This was after we funded them.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
Um, I would almost compare it to getting into the military and boot camp, where, you know, the government probably wants you to not get too messed up.
- MSMichael Seibel
[laughs]
- DCDalton Caldwell
So like basically they, they, they have it down to a science of like how far you can push people.
- MSMichael Seibel
And you have to push people.
- DCDalton Caldwell
And you have to push people, and again, they look back on it where like, "Wow, I'm much better."
- MSMichael Seibel
Yes. [laughs] But they can't kill half the people. [laughs]
- 14:31 – 15:54
Viewing the startup journey as an adventure
- MSMichael Seibel
I will say one thing that helps is liking your users-
- DCDalton Caldwell
Yep
- MSMichael Seibel
... and liking the problem that you're solving. I think it's really, really easy to kind of feel sorry for yourself and get in a negative feedback loop when like you're working on something that I guess like maybe your friends or investors or like the internet thinks is a good idea, but you actually don't yourself enjoy it.
- DCDalton Caldwell
Yeah.
- MSMichael Seibel
Another great hack is like working with people you like who you're friends with, right? Like if you're working with people 'cause you're kind of shoved together in this hodgepodge team and you don't really enjoy them, it's harder. It's harder. But like when you can line up working with people you like, working on a problem you're interested in, liking your users, and enjoying hard work-
- DCDalton Caldwell
It's kinda awesome, right? [laughs]
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
Like [laughs]
- MSMichael Seibel
W- win or lose.
- DCDalton Caldwell
Like you said before.
- MSMichael Seibel
Win or lose, you're probably gonna look back and say, "This was one of the most rewarding times of your life."
- DCDalton Caldwell
Yeah.
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
Well, it's an adventure.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
And I think a lot of people, not everyone-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... but a lot of people would love to go on an adventure.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
[laughs]
- MSMichael Seibel
Yes.
- DCDalton Caldwell
And how many times in your life can you say that you went on an adventure?
- MSMichael Seibel
Yes. And how many of your friends ever get to go on an adventure? And like you're on this adventure now.
- DCDalton Caldwell
Love it.
- MSMichael Seibel
If you're spending the whole time on the adventure waiting for it to be over-
- DCDalton Caldwell
That's not the right feeling. All right,
- 15:54 – 17:21
The unfair advantage of great founders
- DCDalton Caldwell
so what's your last word for founders here? Yeah, I mean, I think it's to realize that this is a learnable skill.
- MSMichael Seibel
Yes.
- DCDalton Caldwell
And that you can, with intention-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... reframe your daily experiences that you might currently be framing as-
- MSMichael Seibel
Yes
- DCDalton Caldwell
... "I can't wait till this is over."
- MSMichael Seibel
Yep.
- DCDalton Caldwell
"I'm suffering."
- MSMichael Seibel
Yep.
- DCDalton Caldwell
"Oh, I, you know, I need this milestone to happen, and then I can finally-
- MSMichael Seibel
Yeah
- DCDalton Caldwell
... enjoy myself." Like if you're telling yourself any of those stories, I'm encouraging you to reframe all those things and to start telling your brain positive stories, that you're learning a lot and you're pushing yourself really h- hard, and you're really proud of that.
- MSMichael Seibel
Yeah.
- DCDalton Caldwell
And that the better you get at this skill to turn discomfort into motivation or like fun, basically-
- MSMichael Seibel
Yeah
- DCDalton Caldwell
... you'll become an unstoppable force.
- MSMichael Seibel
And like maybe the secret for people who made it this far in the video is the founders who've done great things that you admire, and maybe you admire their strategy, you admire their tactics or what they built, this is probably one of their hidden advantages that you don't see. And especially for the founders who stick with it for like a decade, two decades, this is really one of their secret advantages that anyone can grab.
- DCDalton Caldwell
Yep.
- MSMichael Seibel
Awesome. Great chat. All right. Thanks, Michael. [upbeat music]
Episode duration: 17:21
Install uListen for AI-powered chat & search across the full episode — Get Full Transcript
Transcript of episode Bsxa_Yg1Xcw