Most Important Lifestyle Habits Of Successful Founders

1. 0:00 – 0:35

   Introduction

   1. DCDalton Caldwell0:00

      Let's examine the facts.

   2. MSMichael Seibel0:02

      Yes.

   3. DCDalton Caldwell0:02

      Fact, fact, fact, fact. Great. You're fine.

   4. MSMichael Seibel0:06

      Yes.

   5. DCDalton Caldwell0:07

      However, sometimes we look at the facts, and you're not fine. [upbeat music]

   6. MSMichael Seibel0:14

      This is Michael Seibel with Dalton Caldwell. In our last video, we talked about the setbacks that make founders feel like shit when running their startups. And this time, we're gonna talk about how to prevent these punches to the face and how to take a punch and recover if you absolutely must. So Dalton, I think the cool way to think about this is a little

2. 0:35 – 1:50

   Plan for the punches

   1. MSMichael Seibel0:35

      bit like healthcare. There's preventative healthcare, and then there's, you know, treatment. So let's start with the preventative, and, and let's set the, set the framework here. Like, a lot of times founders get punched in the face as almost unforced errors. It's like a result of magical thinking or like other parts of their lives not being set up. And so here are things you can do to either reduce the number of punches that come or at least reduce their intensity 'cause you have your other shit locked up. Does that make sense?

   2. DCDalton Caldwell1:06

      Yeah, exactly. It, it's like, as we spoke to last time, you can't think that you're not gonna have any setbacks, and you're not gonna, again, take some punches. [chuckles] It's gonna happen to you 100%. The, the highs are high, and the lows are low. And so rather than assuming you can be so smart that you will never have low lows, instead, plan ahead. [chuckles] Put the-

   3. MSMichael Seibel1:28

      Yeah

   4. DCDalton Caldwell1:28

      ... put the infrastructure in place so that when you do have these, these big challenges or these low moments, you have the infrastructure set up that, um, you know, you, you planned ahead for it. I think that's very, a very good idea.

   5. MSMichael Seibel1:42

      So we were joking when we were talking about what to talk about in this video. A lot of these things could be put in the category

3. 1:50 – 3:07

   Adulting harder

   1. MSMichael Seibel1:50

      of adulting, and it might turn out that if you want to be a founder of a very successful company, you might have to adult harder than the people around you. [chuckles] In fact, it almost assuredly requires adulting harder than the people around you. Sometimes I think founders look at us, and they're kind of like, "Well, you know, my roommates don't do this, so why do I have to?" And it's like, well, if your roommates aren't trying to build a billion-dollar company, then they don't have to. But maybe you need to be better than the people around you to do something extraordinary.

   2. DCDalton Caldwell2:23

      It's yet another thing that distances you from your peers. And if you-

   3. MSMichael Seibel2:27

      Yes

   4. DCDalton Caldwell2:27

      ... if your whole thing in life is, "I'm the same as my peers, and I'm the same as my roommates that have jobs at, like, big tech companies," er. [chuckles]

   5. MSMichael Seibel2:34

      Nope. [chuckles]

   6. DCDalton Caldwell2:35

      This is yet another-

   7. MSMichael Seibel2:36

      Nope

   8. DCDalton Caldwell2:36

      ... way that you're gonna be isolated and different and have to learn to love that and not-

   9. MSMichael Seibel2:41

      Yes

   10. DCDalton Caldwell2:41

       ... feel sad that when they're like, "Hey, we're gonna go pull another all-nighter, or we're gonna go party Thursday, Friday, Saturday," you have to be cool with opting out of that, right?

   11. MSMichael Seibel2:53

       Yep.

   12. DCDalton Caldwell2:53

       But if you-

   13. MSMichael Seibel2:54

       Yep

   14. DCDalton Caldwell2:54

       ... if you think you can have it all...

   15. MSMichael Seibel2:57

       You can't.

   16. DCDalton Caldwell2:57

       I don't know if you can have it all.

   17. MSMichael Seibel2:59

       You can't. We're here to tell... We're, we're here to ruin that have-it-all dream. [laughs]

   18. DCDalton Caldwell3:04

       [laughs]

   19. MSMichael Seibel3:05

       So where I like to start is

4. 3:07 – 4:05

   Audit how you live

   1. MSMichael Seibel3:07

      audit how you live. Like, think about where you're waking up in the morning. You know, did you get enough sleep? Are you in a, a, a place that's a home? Is it, it... Are you living in a place that makes you more powerful or less powerful? Are you sacrificing? Like, are you losing hit points at home, you know? And, and if that's happening, man, that's unforced error, right? Like, so that's who you're living with, what you're eating. Do you have easy access to exercise? Are... You know, are you living in a place with a bunch of alcohol and drugs everywhere? You know, not helping you. Like, at the minimum, your home should be neutral, but I think for the most successful people, the home's actually a plus. Like, the home is, like, where they're making points, where they're winning points, and I think that a lot of founders in their early days don't understand how much they could be losing based on just how they're living.

   2. DCDalton Caldwell4:03

      Yeah, I think

5. 4:05 – 7:23

   Good & Bad Habits

   1. DCDalton Caldwell4:05

      almost from a clinician's perspective, when someone is having issues, the first thing you look at is sleep disruption, [chuckles] diet, and exercise, right? If you go, if you go look at, you know, research depression or anxiety and things, that's usually where the 80/20 solution is for a lot of folks that are struggling is you look at their sleep patterns. Are they sleeping okay? Are they eating okay? Are they getting exercise? Are they getting sun? All these sorts of things. And so if you don't have your house in order on those fronts, you are not... Even if you don't currently have depression, you are not well-situated to deal with really hard things that might happen to you, right?

   2. MSMichael Seibel4:48

      But Dalton, I went to an Ivy League school, and it was really hard, and I went to a really challenging high school, and I didn't have to change these things to get good grades or to get the good internship. Like, I, you know, I was able to, like, work hard and play hard. Why do I have to change now? It's working. It's working for me, this lifestyle.

   3. DCDalton Caldwell5:11

      I think it, I think it can work for people. You and I know people that, um, certainly don't follow this advice, and they still, still did okay. I just think you and I also know the same people where eventually you've gotta pay the piper. [chuckles]

   4. MSMichael Seibel5:26

      [chuckles]

   5. DCDalton Caldwell5:26

      Like, at some point, no matter... It's almost like you're going into debt, like personal health debt or whatever you wanna call it. And man-

   6. MSMichael Seibel5:33

      Yes

   7. DCDalton Caldwell5:33

      ... you can go pretty far into debt. You can go five years into debt. You can go 10 years into debt. I don't know. But at some point, the debt comes due, um, where you can't hold it all in anymore. You can't hold the whole world on your shoulders. And I think what we're just trying to say is if you start off with good habits early, you're not gonna incur this massive debt that one day causes you to have, like, um, a breakdown or a meltdown or, again, what do you wanna, whatever you wanna call it.

   8. MSMichael Seibel5:59

      Well, and to double down on that, I might argue that, like, you probably can sacrifice these things for five years, like maybe even seven years The tricky thing is that, like, the best companies last multiple decades. The tricky thing is, is the shit that you can get away with in your 20s, you can't get away with in your 30s. [laughs] And company running just gets harder. And so I think sometimes people are like, "Oh, this is gonna be a relative sprint." But it's like, what I like to talk to you about w- with YC founders a lot is like, what happens if this works? Like, are you set up for this to not work, or are you set up for this to work? 'Cause if [laughs] this works, like, woo, you're gonna be in it. Like, you're gonna be in it for a while. And I think sometimes people set their lives up for it to, like, not work, and then wow, you know?

   9. DCDalton Caldwell6:46

      Yeah.

   10. MSMichael Seibel6:46

       Self-fulfilling prophecy.

   11. DCDalton Caldwell6:47

       And when you think about it-

   12. MSMichael Seibel6:49

       You know?

   13. DCDalton Caldwell6:49

       ... this isn't an age thing, this is a lifestyle thing.

   14. MSMichael Seibel6:52

       No. Yeah.

   15. DCDalton Caldwell6:52

       'Cause you'll see, like, 19-year-olds with all the good habits, and you'll see folks that aren't 19 that, like-

   16. MSMichael Seibel7:00

       Yeah

   17. DCDalton Caldwell7:01

       ... uh, still live like 19-year-olds. [laughs] And so this isn't an age thing at all.

   18. MSMichael Seibel7:04

       Yeah.

   19. DCDalton Caldwell7:04

       This is a habits thing, man.

   20. MSMichael Seibel7:06

       Yeah. Well, and you'll even see successful people with good habits lose them, and then wonder why they can't succeed again, right? It's like even just having these habits doesn't mean you keep 'em. Uh, so okay, so that's the- that's, that's your, you know, physical lifestyle set up. You want to talk about

6. 7:23 – 9:22

   Information diet

   1. MSMichael Seibel7:23

      this kind of social media piece, 'cause I think that a lot of people don't understand how toxic social media [laughs] is like...

   2. DCDalton Caldwell7:32

      Yeah. I think, I think you just wanna look at your information diet. The metaphor I think about this stuff with is, um, the same way we have a food diet and, like, of course what we eat and drink affects our moods and how we feel, I actually think the information we consume affects us. And if you think about, again, like myself, all of us, you know, when, when it's a really heavy time in history, when there's a lot going on, when I'm doom scrolling all the time reading about pandemic news or war news or whatever, of course that affects my state of mind, okay? And so to some extent, you can't completely stick your head in the ground about what's going on in the world. No one's saying to do that. But to the extent your social media habits make you feel bad or compare yourselves to people, or say you follow a lot of, like, investors and everything they're talking about is the investment market and who's raising and all of that, and this is just every day you're bombarding your brain with stuff about investor shit. Why? Why is that good? Why- how is that helping you actually run your startup reading what a bunch of investors say about the market all the time?

   3. MSMichael Seibel8:42

      And I think people are surprised that, like, successful founders, like, explicitly block social media. They do crazy things like bl- you know, they, they grayscale their phone so it looks less interesting. They turn off notifications. They're aggressive users of, like, um, [clicks tongue] screen time, like tracking. Like they, they actually pretty aggressively audit this stuff.

   4. DCDalton Caldwell9:03

      So that illiquidity saved you all. And so again, so if you're consuming, if you're consuming media every day and you're reassessing the value, like if you're too paying attention to this stuff-

   5. MSMichael Seibel9:15

      Yeah

   6. DCDalton Caldwell9:15

      ... it doesn't make you make better financial decisions, does it?

   7. MSMichael Seibel9:18

      No.

   8. DCDalton Caldwell9:18

      Isn't that wild?

   9. MSMichael Seibel9:20

      The next area I like to talk

7. 9:22 – 12:51

   Salary bump

   1. MSMichael Seibel9:22

      about is salary. Um, oftentimes, and, and this is more f- of course for companies that have raised funding, just a, a, small incremental 5 or 10% cal- salary bump can make a huge lifestyle difference, and, and it's almost always worth it. Like, I think people screw up, and, and this is where I say to founders, I'd love to hear your advice. If your startup salary is allowing you to save money, it's probably not good, right? You shouldn't be sitting here, like, with Google employee level savings running your startup. However, if your startup salary is giving you the lifestyle that allows you to be all in on your startup because the real world isn't distracting you negatively, um, then it is good. And what's interesting is that often for different founders, this is a different salary level, you know?

   2. DCDalton Caldwell10:18

      Yeah.

   3. MSMichael Seibel10:18

      Perfect example, when I was starting, I had student loans in college. My co-founders didn't. I made a little bit more money so that I wasn't, like, going into debt with my student loans, and that was perfectly reasonable. And no one was like, "Oh, well, you need to take X percent less because you need to pay a $200 student loan every month." It's like, no. Like, so sometimes small changes in salary... Now, you know, if you have a co-founder where it's like, "I need to make a half a million dollars a year, and I'm 23," yeah, that's probably different. But, like, sometimes people are sacrificing penny-wise, pound-foolish, right?

   4. DCDalton Caldwell10:49

      Yeah.

   5. MSMichael Seibel10:49

      Like, sometimes people are being penny-wise, pound-foolish.

   6. DCDalton Caldwell10:51

      I think this is one of those topics, also like equity, where what founders want to hear is, "Here's the right answer. One size fits all for everyone," or, "Here's the formula."

   7. MSMichael Seibel11:02

      Yeah.

   8. DCDalton Caldwell11:02

      "Oh, here's a spreadsheet. Here we go, Michael."

   9. MSMichael Seibel11:05

      [laughs]

   10. DCDalton Caldwell11:05

       "Here's how much to pay yourselves. Just fill out the spreadsheet and we're done." Like, and sadly, like many things in life, anyone that tells you there's simple answers is probably trying to sell you something, you know? Like-

   11. MSMichael Seibel11:16

       [laughs]

   12. DCDalton Caldwell11:17

       Like, like, right? They're like, yeah, it's probably snake oil. And, and, and so the subtlety that I agree with you on is you wanna pay yourself enough that you don't get into debt. You wanna pay yourself enough so that you're properly motivated. You also wanna keep enough, you wanna keep the money in the company. Like, these are all variables that you have to turn, and, you know, if you're gonna be a successful founder, you have to have good judgment, and you have to have opinions. And so when founders have no opinion about this stuff, it's not a great sign. So it's kind of like you need a philosophy of what you're solving for around compensation. You wanna set everyone up for success.

   13. MSMichael Seibel11:55

       Yes.

   14. DCDalton Caldwell11:56

       Align incentives well, and also realize that this, this looks different for every company, man. Like, a lot of folks ask me, "Well, how much should I pay employee number one?" I'm like, "That's a nonsensical question. Who are they? What's..." You know, [laughs] do you see what I'm saying?

   15. MSMichael Seibel12:09

       Exactly.

   16. DCDalton Caldwell12:09

       Like it's-

   17. MSMichael Seibel12:10

       Yeah

   18. DCDalton Caldwell12:10

       ... like, what they want is some answer. "Oh, you should pay employee number one X." But like, no, man. That's like-

   19. MSMichael Seibel12:15

       No

   20. DCDalton Caldwell12:15

       ... that i- that's not how this works.

   21. MSMichael Seibel12:18

       It was almost easier to come to these conclusions when I think back, 'cause we didn't have very much money [laughs] and so we kinda had to like- It does make it easier ... you know, like whenever anything is scarce, you have to ration it more effectively. And I think that, like our philosophy, 'cause I, I like what you're saying, there's no formula, but we had a philosophy which is like salary is for living and equity is for upside. Like that's, that was the kind of philosophy. Um, and, and I think that served us, that served us pretty well. Um, [lip smack] the next area of prevention, you

8. 12:51 – 16:37

   Hard conversations

   1. MSMichael Seibel12:51

      have to learn how to have hard conversations with your co-founders and for everyone to be okay afterwards. Um, and everyone has to go through this, and it's gonna suck, but if you have some of those in the bag, when you get punched in the face, y'all know a little bit more how to interact with each other. And to me, the biggest challenge that I've seen on this front, and we've talked about this at YC quite a bit, is this, um, anxious personality type versus avoidant personality type. You know, when people are challenged, people are frustrated, and this is a way oversimplification, but sometimes people are anxious. They wanna deal with the problem right now. They're leaning in. They wanna talk for... They've talked for two hours with you, and they wanna talk for another two hours with you. And sometimes people are avoidant and, you know, after five minutes, they're done. They, they wanna think about it for a long time. They'd rather talk asynchronously. And I actually see that most problems between co-founders, the root cause isn't whatever went wrong or whatever they're debating. It's actually their style of dealing with their frustration. And if you can have a little empathy if the person who you're working with has a different style of dealing with frustration than you do, and you can just take a beat, right? I'm the, I'm the anxious type. You know this, Dalton. Like I'm super an- I wanna like talk about it for six hours, then six more hours. I wanna plan. I wanna write it down right now. Go, go, go, go now, [laughs] like. And I always get into trouble when I'm interacting with someone who reacts negatively to that, and I always have to kind of be like, "Fuck, I gotta take a beat." Like in this situation, you gotta take a beat. And so in my experience, if you can figure out that dance with your co-founder, it's so much more helpful when you're dealing with these external challenges. And like the startup's gonna present many opportunities for frustration with your co-founder, [laughs] right? Like infinite opportunities. Yeah. It's like the whole topic today, which is eventually you're gonna take punches. You're gonna have setbacks with your startup. Eventually, you're gonna have conflict with your co-founder. 100%. [laughs] Yeah, 100%. Like, like- 100% ... and the thing that you're disagreeing about isn't even a thing. Like who cares? It's noise. [laughs] Yeah. Right? Like, oh, it- it's like roommates. "Oh, did you take, did you put the dishes away?" Or like, like it's not about the thing. Yes. And like it's not about who's right or who's wrong, and it's funny 'cause a lot of people wanna ask us advice about co-founder stuff, but they- what they wanna, what they want is us to agree that they were right and their co-founder's wrong. [laughs] Yeah. We love that. We're like- You're wrong ... "Dalton, can I tell you about this situation? Basically, I'm smart. My co-founder's dumb. What do you think I should do about it?" Like it's always s- [laughs] And it's like, "No, no, no, no, no. I'm not gonna take the bait on that." I'm sure, like the actual thing that you need advice on or thing to work on is the meta conversation, which is like- Yes, yes ... how do you deal with conflict so that people feel good when it's over? Yeah. Otherwise, whatever the, you know, not cleaning up your dishes or taking the trash out, whatever the equivalent of that is in your co-founder relationship, eventually it's not gonna work out, man, right? No. You gotta have tools. No. 'Cause there's gonna be more issues. Well, and I think that's what's fun about this one is that like early stage founders argue about the dumbest things, that there's almost infinite opportunities to practice this dealing with frustration of your co-founder. Like it is like a roommate relationship. There's infinite opportunities before something that's a real whammy comes. So like take those opportunities. Like please take them. Do you have any more on the preventative side before we move to treatment? I think it's just

9. 16:37 – 18:00

   Expectation setting

   1. MSMichael Seibel16:37

      this expectation setting. I think so much of life is expectation setting, where setting expectations for yourself, setting expectations for people you work with about what to expect. If you are good at that, people can deal with all sorts of stuff. And when you get into the biggest trouble, both with yourself, managing your own brain, as well as working with other people, is when you say a bunch of stuff that is, that turns out to be really not true and you set expectations poorly and you have to like dig yourself out of this deep hole that you dug yourself into 'cause you promised a bunch of shit or you set expectations in such a way that just weren't true. And so expectation setting is key for prevention. And you know, we talked about this in another video, but man, it's, it, it helps to study the real story of companies, right? It helps just to just know how long this takes. Man, it, it really helps for you to not have stupid expectations. "Oh, well, this company became a billion dollar company in two years, so that's clearly the average path." And it's like f- no. Like absolutely not. [laughs] Absolutely not. Uh, it's funny because in some ways you're saying sometimes these companies punch themselves out, right? Like they don't even need external forces. They set a stupid expectation. They don't hit their own unrealistic expectation, then they feel like something's wrong, and you're just like, "Holy crap." Like you just invented a crisis. Like [laughs] startups have enough crises without that. [laughs] Well, we've talked about all the things you can do to prevent the injury.

10. 18:00 – 21:08

    Fight or flight

    1. MSMichael Seibel18:00

       Let's say the punch happens, bam, and you need some treatment. Something really bad happens or you suspect something really bad happens. Um, I think the first point that you brought up that I really love is this idea of like, "Do I have to do anything right now?" Like- Talk about that a little bit more.

    2. DCDalton Caldwell18:20

       Yeah. I think I learned this as a founder the hard way, which is when something bad happens, you want to immediately, like, make a move. You wanna, like, call a meeting, or you wanna... You get a, you get an email with bad news in it. You wanna hit respond and, like, in the moment of fight or flight when your adrenaline's pumping, you're like, "How dare you, sir?" You know? [laughs] You wanna-

    3. MSMichael Seibel18:44

       Yes

    4. DCDalton Caldwell18:45

       ... you wanna, you wanna get- start writing emails with that tone. "Dear sir-"

    5. MSMichael Seibel18:50

       Yes

    6. DCDalton Caldwell18:51

       ... "in response-

    7. MSMichael Seibel18:51

       You wanna punch back

    8. DCDalton Caldwell18:51

       ... to your query about" [laughs] You know. Like, if you're ever typing an email in that tone, like, you know, don't do it. Um, [laughs] that's... And, and what I've noticed is you can just, like, not respond or, like, s- let stuff sit a little bit, and sleeping on it is the minimum thing I would do. This is what I always tell founders, is when they have something happen, to at least sleep on it, 'cause I've just noticed the next day you have a whole new amount of clarity on the situation.

    9. MSMichael Seibel19:26

       And I, and I often find myself in my best moments... In my worst moments, and exactly like you said, I'm like, "Act now. Go. Send that email." Like, "Punch back." In my best moments, I'm always like, if there's ever a decision that feels like it's action one or action two, there's always a third option, which is don't act. There's al- like, and it's almost never presented to you. Um, I find a lot of times lawyers fuck companies with this. It's like, "You gotta do this or that." And it's like, it's not like, "How about we don't respond?"

    10. DCDalton Caldwell19:56

        Yeah. What if we do nothing?

    11. MSMichael Seibel19:57

        [laughs] Yeah.

    12. DCDalton Caldwell19:58

        What if no action's better?

    13. MSMichael Seibel19:58

        What would happen? Yes. And then what's really funny is that, like, the best founders, no action becomes one of their, like, key plays. Like, they use that play way more than you think. [laughs]

    14. DCDalton Caldwell20:12

        It's a great play. It's a great play.

    15. MSMichael Seibel20:13

        Such a good play. [laughs] Um, and it's amazing that, like, for the best founders, no action is, like, you know, 20, 30, 40% of the time what they do, maybe more. But for other founders, they don't even know the play exists. Like, they don't even know the play exists.

    16. DCDalton Caldwell20:29

        Yeah. Maybe just archive the email.

    17. MSMichael Seibel20:31

        Yeah.

    18. DCDalton Caldwell20:31

        Whatever the email says. [laughs]

    19. MSMichael Seibel20:32

        Yeah. That's true.

    20. DCDalton Caldwell20:34

        Just hit archive.

    21. MSMichael Seibel20:34

        You know, it's a really big deal. They'll probably reply back.

    22. DCDalton Caldwell20:36

        [laughs]

    23. MSMichael Seibel20:37

        I've noti- I've noticed this. [laughs] It's a really big deal. Um, and of course, don't do this in the case where someone's health is on the line or someone's gonna go to jail or whatever, right? That, that, that's different. But, um-

    24. DCDalton Caldwell20:47

        Yeah. It's more of, like, the stuff where someone... Where it's, like, interpersonal or someone, I don't know.

    25. MSMichael Seibel20:56

        Yeah.

    26. DCDalton Caldwell20:56

        Someone said something bad.

    27. MSMichael Seibel20:58

        That you, you, you can archive. You, you can wait till the weekend's over to reply to that Slack message. Like, it's gonna... It'll, it'll survive. So the next one on the list is it's okay

11. 21:08 – 24:59

    Good R&R

    1. MSMichael Seibel21:08

       to take a day off. It's okay to go home. I think that, you know, there was one moment in my career where, um, we were gonna get bought, uh, Socam was gonna get bought, and we were two months into the diligence process, and we got a call that said the deal was off. And it was the only moment in my career where I was like, "I'm not gonna react to this well in front of my co-founders."

    2. DCDalton Caldwell21:39

       [laughs]

    3. MSMichael Seibel21:40

       "I just need to go home." [laughs] Like, at least home I can react in a way that won't be a bad example to them. You know? Like, 'cause they're gonna look at my reaction, they're gonna be like, "Are we fucked?" And if I'm looking like we're fucked, [laughs] like, that's not helping, you know? When the general's, like, pulling their hair being like, "This looks horrible. We're gonna die." [laughs] Like, that's not good. That's not good. [laughs] Um, and man, like, going home, um, hanging out with, you know, at the time was my girlfriend, but then, you know, later became my wife. Like, taking that day, the next day I could kind of bring a better Michael to the table.

    4. DCDalton Caldwell22:24

       Yeah. Right.

    5. MSMichael Seibel22:24

       [laughs] You know? Like, that was, that was a big thing. That was a big thing. Um, I, I, I was thinking about this in the context of, like, when things go bad, there's a certain side of pe- set of people you should probably be hanging out with, and a certain set of people you probably shouldn't be hanging out with, right? Like, how, how do you think about that?

    6. DCDalton Caldwell22:44

       Yeah. I mean, again, we... I have my personal experience, and I have all the data points we have across YC Founders. And you just sometimes see people that are, that are taking punches and having a hard time, and there's some really amazing people that you can hang out with that support you and tell you you're okay and validate your experience and, like, let you take space for yourself and, like, all this good stuff. And, like, these are, these are great people to have in your life. And then we see other sorts of folks that are like, you know, "Oh, you should do tons of drugs." [laughs] Um, or, "Hey," like, "Let's go not sleep for a really long amount of time," or, "Let's hang out with celebrities." Or like, you know. Like, there's all these different crowds you can get into, and it's depressing how predictive that is for how people will deal with, like, setbacks, you know?

    7. MSMichael Seibel23:41

       Yeah.

    8. DCDalton Caldwell23:42

       Even... And these are adults. We're not even talking, we're not talking about... These are, these are-

    9. MSMichael Seibel23:45

       These are adults

    10. DCDalton Caldwell23:45

        ... these are our-

    11. MSMichael Seibel23:47

        Grown people

    12. DCDalton Caldwell23:47

        ... our age people-

    13. MSMichael Seibel23:48

        [laughs] Yeah

    14. DCDalton Caldwell23:49

        ... still struggle with this particular one. Um, and so I think you just wanna think about, yeah, who, who you're spending time with when you're, when you're taking punches and what kind of habits that you're taking from the peer group.

    15. MSMichael Seibel24:04

        You know what? Man, I really think that the best people... You know, I'll be explicit, right? The best people, shit goes wrong, and they go take a hike or something, and the worst people think, shit goes wrong, and they drink and do drugs. And, like, it tends to be that those friend groups You know, for a lot of founders, you know the friends who if you go out with them, you're gonna drink and do drugs, and you know the other friends where if you go out with them, you're gonna go on a hike. Like, just explicit, you know? And, you know, but pick the right group for- [laughs] You know, pick the right group. Um, and it's weird because I don't think the friends are bad. They're not trying-

    16. DCDalton Caldwell24:40

        Yeah

    17. MSMichael Seibel24:40

        ... to harm you, you know?

    18. DCDalton Caldwell24:42

        Well, d- they're doing their own thing.

    19. MSMichael Seibel24:44

        Yeah.

    20. DCDalton Caldwell24:44

        Yeah.

    21. MSMichael Seibel24:46

        Um, it's just that, you know, you have to choose the right therapy. You have to choose the right therapy for yourself. And, and actually, this, that's a good segue. Like, let's talk about real

12. 24:59 – 26:50

    Healthcare

    1. MSMichael Seibel24:59

       healthcare. Let's talk about mental healthcare for a second. Like, you know, this is st- this is becoming less of a controversial issue, but I still think that it's something that needs to be normed more, right?

    2. DCDalton Caldwell25:10

       Yeah. I mean, therapy is good. Medication is good if you're prescribed it and it's not from your friend. Just kidding. Um [laughs]

    3. MSMichael Seibel25:20

       [laughs]

    4. DCDalton Caldwell25:21

       Uh, you know, this is... This stuff is de-stigmatized, and it's, it's important. And like a lot of founders struggle. I think it's the ups and the downs exacerbate this stuff. And again, the stuff I said earlier, um, sleep disruption, stress, all these other things exacerbate it. So, you know, sometimes that is the appropriate thing to do here, so you should do it and not think you're too tough or, or whatever, whatever reason it would be that you wouldn't use these things as a, as a crutch. I just... I've noticed the people that aren't, the people that aren't willing to use this stuff, they find other crutches that, again, I would not recommend.

    5. MSMichael Seibel25:58

       They do.

    6. DCDalton Caldwell25:59

       Right?

    7. MSMichael Seibel25:59

       Well, and I think that most people don't realize this isn't the kind of stuff that, that comes out in your favorite company's press release. Most people don't realize how the founders who they are impressed with actually take advantage of therapy, actually take advantage of medication. Most people don't realize, you know, there are founders I know who've sworn off drinking 'cause, like, they are not good. You know? They, they, they're not the best version of themselves when they're drinking. Like, this isn't the kind of stuff that people will talk about very publicly, but we know a lot of people, and when someone's trying to squeeze every ounce of positive productivity out of themselves, sometimes like, you know, um, they need to use these tools, and it's really helpful. Really, really helpful. So, you know, let's talk about the

13. 26:50 – 32:00

    Fatal punches

    1. MSMichael Seibel26:50

       fatal punches, right? You know, at YC we deal with a lot of failure. We deal with a lot of companies who fail, and you and I have to have a lot of conversations with founders who their company has failed, and their first thought is, "I'm a failure." They personalize that failure. What are the some of the things you tell those people when they're dealing with that fatal punch?

    2. DCDalton Caldwell27:11

       Yeah. I think it, as per what we talked about here, a lot of the things that people think are game over aren't, and so our advice is, "Don't give up." Like, you actually have a bunch of customers. You have a bunch of money in the bank. Like, let's look at the facts. You're good. And so a lot of our office hours are, "Let's examine the facts. Fact, fact, fact, fact. Great. You're fine." However, sometimes we look at the facts and you're not fine.

    3. MSMichael Seibel27:38

       Not good.

    4. DCDalton Caldwell27:38

       And it doesn't help you... Like, you don't need a pep talk to keep going, and it actually is probably the right thing for you to not keep going. Because at the end of the day, this is your life. You only have one of them, and messing up your life in a permanent way, [laughs] your savings, your family, your friends, whatever it is, you know, don't do that. And again, I know it can be confusing out there 'cause we get bombarded with messages, "Oh, but you say you never give up," or you say... You know? Like, yeah. It's confusing.

    5. MSMichael Seibel28:10

       It's not that easy.

    6. DCDalton Caldwell28:11

       It's not that easy.

    7. MSMichael Seibel28:11

       Yeah, it's complicated. Yeah.

    8. DCDalton Caldwell28:13

       It's complicated. So I think you need to actually, with as clear, objective ways as you can, be able to know when it's not working, and that it was a fatal punch, and that, yeah, you should not do this anymore. Like, somet- sometimes you see people get into, like, debt where they owe a bunch of people a lot of money, and then they shut down, and they ripped off all their suppliers. Again, you know, you know what I'm trying to say? Like, like, you-

    9. MSMichael Seibel28:41

       Not good

    10. DCDalton Caldwell28:42

        ... you fail in such a way that you hurt a bunch of people, not just yourself.

    11. MSMichael Seibel28:46

        Not good.

    12. DCDalton Caldwell28:47

        Don't do that.

    13. MSMichael Seibel28:48

        Well, and I think that this is what's tricky is that I think someone needs to be out there saying that these aren't the things you have to put on the table to win. Yes, when you're working hard, you're gonna probably have to spend less time with your family or friends, but you don't have to put those relationships, you don't have to sacrifice those relationships to win. In fact, they're a source of strength. You're working hard. You're probably not saving as much money as you would be if you're working another job, but you don't have to sacrifice all your savings. You don't have to go into extreme debt. Like, if you're working hard, like, you might not be able to get the salary that allows you to live in the apartment of your dreams. But, like, if you have to crash on friend's couches, these things don't tend to have to be sacrificed to win. And so if you're, if you're taking these kind of one-way hard life hits, maybe the facts are, are, are set up.

    14. DCDalton Caldwell29:40

        Yeah. And again, what's tough is when you're one of those folks, sometimes you can even be victimized by people that'll, like, keep bleeding you because that's their racket. And we see this a lot with struggling startups. All sorts of people will come out of the woodwork to sell you services or promise they'll connect you with the investors, or they'll help you fundraise, or you name it. And it's like, it's kind of like moving to Hollywood to become an actor and it's not going well. All these people will... Like, there's a whole underbelly of folks who exist to kind of-

    15. MSMichael Seibel30:13

        To sell you stuff

    16. DCDalton Caldwell30:13

        ... rip off-

    17. MSMichael Seibel30:14

        Yeah

    18. DCDalton Caldwell30:14

        ... the people who aren't doing well.

    19. MSMichael Seibel30:17

        You know, to me, where I see this happen that's most tragic is with non-technical founders because it'll be some dev shop or some, you know, they're like, "If you give me your last dollar, I promise that I'll solve your problem." And it's like, "Uh..."

    20. DCDalton Caldwell30:33

        Yeah, and you see people writing checks for 20, 30, 40, whatever, 50 grand out of their personal checking account, their life savings, to some dev shop-

    21. MSMichael Seibel30:41

        Yes

    22. DCDalton Caldwell30:42

        ... that's, like-

    23. MSMichael Seibel30:43

        Yes

    24. DCDalton Caldwell30:43

        ... their whole business model is to rip... I shouldn't say rip off, but, like, they're like, "Yeah, cool." Like, "Whatever." Like, "J- as long as the check clears, we'll do it," you know?

    25. MSMichael Seibel30:50

        Yeah. Yeah.

    26. DCDalton Caldwell30:50

        It's pretty depressing.

    27. MSMichael Seibel30:52

        It's really depressing. And, and I think that, like, those founders when we have this conversation be like, "Hey, your startup failed. That doesn't mean you failed." You know? Sometimes they just need to hear someone say that. Like, so often we'll talk about, like, "Look at this person. Their startup failed, and they have another one that does well. Look at this person. Their startup failed, and they're now working as an executive at this really cool company." Like, these experiences you have are valuable to you even if your company didn't work, [laughs] you know? You learned 10X more than you would've learned otherwise even if your company didn't work. And sometimes when we explain that silver lining, people are like, "Oh. Oh, you're right." You know? Th- that's actually a fun part of the job. So there you go. Step one, how to try to avoid the punches or, and step two, when they come, how to recover as fast as possible. Great chatting today, Dalton. Thanks, man. [upbeat music]

Episode duration: 32:00