Skip to content
Dalton + MichaelDalton + Michael

Want to Build a Great Startup? Start Having Fun.

The best startup founders have a secret advantage: they have fun. Dalton and Michael discuss how you can embrace "Type 2 Fun" and enjoy the adventure. It's not just a mindset, it's a requirement to build an enduring company. Discussion includes: the difference between type one and type two fun, why type two fun is more rewarding than “empty calorie” fun, how reframing hard days as fun unlocks endurance, why people fondly remember their hardest startup moments, how to tell if you’re a replaceable employee, why learning to love being uncomfortable is how you stretch yourself, how to transfer grit from sports or academics to your startup, why a competitor who is having a great time is the hardest to beat, why you shouldn’t wait for the torture to end, why people suited to be founders are under-stimulated by normal work, the personal inventory founders should take (rent, safety, sleep, food, exercise) before pushing hard, why liking your users, your problem and your teammates helps, and why the startup journey is an adventure worth enjoying. 0:00 Introduction to type two fun 1:53 Learning to enjoy hard things 4:34 The mindset shift in startups 5:41 Learning to love being uncomfortable 6:53 Transferring grit from life to startups 8:38 The competitive edge of type two fun 11:01 Flipping the mindset switch 12:10 Seeking challenge vs. seeking comfort 13:08 Maintaining a healthy foundation 14:31 Viewing the startup journey as an adventure 15:54 The unfair advantage of great founders _ Dalton + Michael is brought to you by @Standard_Cap. Standard Capital is the AI-native Series A fund. Learn more at standardcap.com – About Dalton: Dalton Caldwell is Co-Founder and Partner of Standard Capital. He spent 12 years at Y Combinator, where he served as Managing Partner, worked across 25 YC batches, and advised more than 1,000 startups. His investments include Whatnot, Brex, GitLab, PostHog, Stock Space, Rappi, Razorpay, and Oklo. Before becoming an investor, Dalton founded imeem and App.net. About Michael: Michael Seibel is a Partner Emeritus at Y Combinator, where he served as Managing Partner of the early stage accelerator from 2014 - 2024. Michael also serves on the board of three companies: Reddit, Dropbox, and Kalshi. He moved to the bay area in 2006, and was a co-founder and CEO of two Y Combinator startups Justin.tv/Twitch (2007 - 2011) and Socialcam (2011 - 2012). In 2012 Socialcam sold to Autodesk Inc. for $60m and in 2014, under the leadership of Emmett Shear (CEO) and Kevin Lin (COO) Twitch sold to Amazon for $970m. – Are you an AI builder? Check out StandardDB. Discover offers, credits, tools, and partner programs from the StandardDB ecosystem.

Michael SeibelhostDalton Caldwellhost
Oct 12, 202617mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 1:53

    Introduction to type two fun

    1. MS

      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?

    2. DC

      Yeah, let's start with definitions. We're gonna be talking about hard work today.

    3. MS

      Mm.

    4. DC

      And so-

    5. MS

      For all you startup founders-

    6. DC

      [laughs]

    7. MS

      ... you, you, you should leave, 'cause, like-

    8. DC

      It's hard work

    9. MS

      ... startups are hard work. [laughs]

    10. DC

      Um, and so look, let's start with type one fun. Type one fun is something that is fun-

    11. MS

      Yeah

    12. DC

      ... while you're doing it.

    13. MS

      Like ice cream.

    14. DC

      Ice cream is fun.

    15. MS

      Yeah.

    16. DC

      That's type one fun.

    17. MS

      Yeah.

    18. DC

      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."

    19. MS

      Going to the gym.

    20. DC

      [laughs]

    21. MS

      [laughs]

    22. DC

      Climbing a mountain. Any kind of, like, intense-

    23. MS

      Yeah

    24. DC

      ... 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-

    25. MS

      Yes

    26. DC

      ... in the moment, you're like, "Man, this is hard."

    27. MS

      Yes.

    28. DC

      And then you look back at it wistfully and you wish you were there, because it was super fun in retrospect.

    29. MS

      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]

    30. DC

      And so, you know, you and I used to give a talk at the start of every YC batch-

  2. 1:53 – 4:34

    Learning to enjoy hard things

    1. MS

      Yeah.

    2. DC

      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-

    3. MS

      Yeah

    4. DC

      ... that was really, really hard-

    5. MS

      Yeah

    6. DC

      ... and realize it was the most fun thing you have ever done in your entire life.

    7. MS

      [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.

    8. DC

      Yep.

    9. MS

      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.

    10. DC

      [laughs]

    11. MS

      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?

    12. DC

      They talk about how much they miss or, like, how fondly they remember doing really hard things. [laughs]

    13. MS

      [laughs]

    14. DC

      And being a part of a really small team.

    15. MS

      Yes.

    16. DC

      And even if it doesn't work out, people look back at these memories-

    17. MS

      Yes

    18. DC

      ... as, as precious. Again, I think we're arguing this is a skill that you could learn.

    19. MS

      Yes.

    20. DC

      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."

    21. MS

      Yep.

    22. DC

      "And wow, I didn't sleep at all, and I didn't take care of myself, and we were just suffering the whole time."

    23. MS

      Yep.

    24. DC

      Or you could say, "Wow, this is, like, the coolest thing I've ever done." [laughs]

    25. MS

      Yes, yes, yes.

    26. DC

      "This is the most highly leveraged point of my life."

    27. MS

      Yes, yes.

    28. DC

      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-

    29. MS

      Yes

    30. DC

      ... if you choose to have fun.

  3. 4:34 – 5:41

    The mindset shift in startups

    1. MS

      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."

    2. DC

      Yeah.

    3. MS

      "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?

    4. DC

      Yeah.

    5. MS

      Like-

    6. DC

      This is really living.

    7. MS

      Exactly.

    8. DC

      Yeah, yeah, yeah.

    9. MS

      Like, I'm alive.

    10. DC

      Yes, exactly.

    11. MS

      [laughs]

    12. DC

      'Cause, like-

    13. MS

      Right

    14. DC

      ... 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.

    15. MS

      You're ma-

    16. DC

      You-

    17. MS

      You're taking no risks.

    18. DC

      Yeah.

    19. MS

      You're, you're just kinda like-

    20. DC

      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.

  4. 5:41 – 6:53

    Learning to love being uncomfortable

    1. DC

      I think the way that I would always talk about this in office hours is to learn to love being uncomfortable.

    2. MS

      [laughs]

    3. DC

      And that human beings are naturally, you know, homeostasis, right? We're always-

    4. MS

      Yes

    5. DC

      ... seeking comfort.

    6. MS

      Yes.

    7. DC

      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-

    8. MS

      Yes

    9. DC

      ... like, you know, many jobs-

    10. MS

      Yes

    11. DC

      ... it involves being very comfortable.

    12. MS

      Mm-hmm.

    13. DC

      You know, comfortable seats, comfortable desks. Nothing unexpected ever happens. You know, they do your laundry for you at the office. They-

    14. MS

      That's almost the def-

    15. DC

      ... cater lunches

    16. MS

      ... 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.

    17. DC

      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-

    18. MS

      Yeah

    19. DC

      ... and find it fun, and seek uncomfortable-

    20. MS

      Yes

    21. DC

      ... that's actually how you stretch yourself to do fantastic work. And the number one way to get good at sales, for instance-

    22. MS

      Yeah

    23. DC

      ... is to get comfortable just doing a lot of sales and getting-

    24. MS

      Yes

    25. DC

      ... having people tell you no a lot, and getting rejected.

    26. MS

      Yes.

    27. DC

      And you learn to kind of love it.

  5. 6:53 – 8:38

    Transferring grit from life to startups

    1. MS

      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.

    2. DC

      And think about it. In those experiences, what actually made you better?

    3. MS

      It's the time grinding.

    4. DC

      It's, like, the pain.

    5. MS

      Yes. [laughs]

    6. DC

      It's basically you only get better-

    7. MS

      Yes

    8. DC

      ... if you push yourself to failure.

    9. MS

      Exactly.

    10. DC

      If you push yourself to, you know, your body having to react.

    11. MS

      Yes.

    12. DC

      Right? [laughs]

    13. MS

      Yes. That's where all of the value comes in that moment.

    14. DC

      And again, that, and these people aren't suffering, right? Like they-

    15. MS

      No

    16. DC

      ... like-

    17. MS

      No

    18. DC

      ... they love playing the game. [laughs]

    19. MS

      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?

    20. DC

      Yeah.

    21. MS

      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-

    22. DC

      Right

    23. MS

      ... stretched yourself and you didn't think you could do it?

  6. 8:38 – 11:01

    The competitive edge of type two fun

    1. MS

      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-

    2. DC

      Well-

    3. MS

      ... I'll work hard and let me figure out the hack. Let me-

    4. DC

      The-

    5. MS

      ... figure out the cheat.

    6. DC

      Why did we give this talk at the beginning of the batch?

    7. MS

      Yes.

    8. DC

      We gave this talk because too many people thought, "I got into YC."

    9. MS

      Hard work's done.

    10. DC

      "Now I can be comfortable. I've done it."

    11. MS

      [laughs]

    12. DC

      "Like, we made it," right? Like, "Oh, I'm on easy street."

    13. MS

      [laughs]

    14. DC

      "What, you know, I got into YC." And we're like, "Hey, folks. Bad news."

    15. MS

      Ooh. [laughs]

    16. DC

      "We, we have some tough news to tell you."

    17. MS

      Oh. [laughs] Boo.

    18. DC

      Like, if that's your mentality, you are not gonna make it.

    19. MS

      No. [laughs]

    20. DC

      And instead, we invite you to learn to embrace doing really uncomfortable things and do it in an environment with peers.

    21. MS

      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.

    22. DC

      Yeah.

    23. MS

      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."

    24. DC

      [laughs]

    25. MS

      "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.

    26. DC

      Yeah. It, it's almost like, um, you know, plants turn sunlight into energy, you know, photosynthesis.

    27. MS

      Yes.

    28. DC

      Um, great founders turn being uncomfortable into motivation, and in turn, it fuels them.

    29. MS

      Yes.

    30. DC

      They're like, "Yeah." [laughs]

  7. 11:01 – 12:10

    Flipping the mindset switch

    1. DC

      time.

    2. MS

      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-

    3. DC

      It's 'cause it's not torture. [laughs]

    4. MS

      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-

    5. DC

      Yeah, it's all not true. Sorry

    6. MS

      ... they're like, yeah, like they're like, that's like the, the, they're getting pummeled by the rock. [laughs]

    7. DC

      Yeah.

    8. MS

      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.

    9. DC

      That's the key, is I think this is a learnable skill.

    10. MS

      Yes.

    11. DC

      I think if you're watching this video-

    12. MS

      Yes

    13. DC

      ... there's, like, a bit in your brain that can flip.

    14. MS

      Yes.

    15. DC

      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."

    16. MS

      Yes.

    17. DC

      "I get this number of users."

    18. MS

      Yes.

    19. DC

      "Or I get into YC," or whatever it is. You can just completely change your mentality.

    20. MS

      Yes.

    21. DC

      And it's your choice to be like, "Wow, I'm having an amazing time. Isn't this fun?"

    22. MS

      Yeah. [laughs]

    23. DC

      And I'm alive.

    24. MS

      Yeah. Yeah. [laughs]

  8. 12:10 – 13:08

    Seeking challenge vs. seeking comfort

    1. MS

      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.

    2. DC

      Mm-hmm.

    3. MS

      And it's, it's not.

    4. DC

      No.

    5. MS

      It's absolutely not.

    6. DC

      They'd be bored.

    7. MS

      It-

    8. DC

      They're under-stimulated.

    9. MS

      Exactly.

    10. DC

      Right? Like a lot of people-

    11. MS

      Exactly

    12. DC

      ... that are well-suited to be founders are under-stimulated doing normal stuff, right?

    13. MS

      That's why th- that's why they're doing founder.

    14. DC

      [laughs]

    15. MS

      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.

    16. DC

      Like-

    17. MS

      And it got you here

  9. 13:08 – 14:31

    Maintaining a healthy foundation

    1. DC

      ... and like look, this is an important piece of context to give when we would, when we would give this talk.

    2. MS

      Yeah.

    3. DC

      Um, it was to wri- remind people that like they are okay and they can take this risks-

    4. MS

      Yes

    5. DC

      ... and to do this little personal inventory.

    6. MS

      Yes.

    7. DC

      And so let's do the little inventory.

    8. MS

      Yeah.

    9. DC

      Do you have enough money to pay the rent?

    10. MS

      Boom.

    11. DC

      Are you personally safe?

    12. MS

      Yes.

    13. DC

      Are you getting sleep?

    14. MS

      Yes.

    15. DC

      Are you eating well?

    16. MS

      Yes.

    17. DC

      Do you have exercise?

    18. MS

      Yes.

    19. DC

      Like basically, we certainly were never like, "Yeah, go, you know, give yourself psychosis and take-

    20. MS

      No

    21. DC

      ... incredible risks."

    22. MS

      No.

    23. DC

      This was after we funded them.

    24. MS

      Yes.

    25. DC

      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.

    26. MS

      [laughs]

    27. DC

      So like basically they, they, they have it down to a science of like how far you can push people.

    28. MS

      And you have to push people.

    29. DC

      And you have to push people, and again, they look back on it where like, "Wow, I'm much better."

    30. MS

      Yes. [laughs] But they can't kill half the people. [laughs]

  10. 14:31 – 15:54

    Viewing the startup journey as an adventure

    1. MS

      I will say one thing that helps is liking your users-

    2. DC

      Yep

    3. MS

      ... 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.

    4. DC

      Yeah.

    5. MS

      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-

    6. DC

      It's kinda awesome, right? [laughs]

    7. MS

      Yeah.

    8. DC

      Like [laughs]

    9. MS

      W- win or lose.

    10. DC

      Like you said before.

    11. MS

      Win or lose, you're probably gonna look back and say, "This was one of the most rewarding times of your life."

    12. DC

      Yeah.

    13. MS

      Yeah.

    14. DC

      Well, it's an adventure.

    15. MS

      Yes.

    16. DC

      And I think a lot of people, not everyone-

    17. MS

      Yes

    18. DC

      ... but a lot of people would love to go on an adventure.

    19. MS

      Yes.

    20. DC

      [laughs]

    21. MS

      Yes.

    22. DC

      And how many times in your life can you say that you went on an adventure?

    23. MS

      Yes. And how many of your friends ever get to go on an adventure? And like you're on this adventure now.

    24. DC

      Love it.

    25. MS

      If you're spending the whole time on the adventure waiting for it to be over-

    26. DC

      That's not the right feeling. All right,

  11. 15:54 – 17:21

    The unfair advantage of great founders

    1. DC

      so what's your last word for founders here? Yeah, I mean, I think it's to realize that this is a learnable skill.

    2. MS

      Yes.

    3. DC

      And that you can, with intention-

    4. MS

      Yes

    5. DC

      ... reframe your daily experiences that you might currently be framing as-

    6. MS

      Yes

    7. DC

      ... "I can't wait till this is over."

    8. MS

      Yep.

    9. DC

      "I'm suffering."

    10. MS

      Yep.

    11. DC

      "Oh, I, you know, I need this milestone to happen, and then I can finally-

    12. MS

      Yeah

    13. DC

      ... 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.

    14. MS

      Yeah.

    15. DC

      And that the better you get at this skill to turn discomfort into motivation or like fun, basically-

    16. MS

      Yeah

    17. DC

      ... you'll become an unstoppable force.

    18. MS

      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.

    19. DC

      Yep.

    20. MS

      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

Get more out of YouTube videos.

High quality summaries for YouTube videos. Accurate transcripts to search & find moments. Powered by ChatGPT & Claude AI.