How Future Billionaires Get Sh*t Done

1. 0:00 – 0:38

   How Future Billionaires Get Sh*t Done

   1. MSMichael Seibel0:00

      I think notebooks are great for ideas. I think like a well-managed to-do list is a software product that you need to adopt, and there's like 80 of them. I actually don't even care which one you adopt, but it's like [laughs] when I like tell something to founders and then they write it down in a notebook, I'm like, "That's gone forever." [laughs]

   2. DCDalton Caldwell0:19

      But they look cool. They have like a fountain pen, and they're like-

   3. MSMichael Seibel0:23

      They do. Yes

   4. DCDalton Caldwell0:23

      ... taking beautiful notes, Michael. Very satisfying.

   5. MSMichael Seibel0:25

      We all know that everything important's in the Moleskine notebook. [upbeat music] This is Michael Seibel with Dalton Caldwell. Today, we're gonna talk about how future billionaires get shit done.

2. 0:38 – 1:18

   PG Essay

   1. MSMichael Seibel0:38

      So Dalton, you were inspired by a PG post when thinking of this idea, right?

   2. DCDalton Caldwell0:44

      Yeah. Paul Graham wrote this really famous blog post, um, [lip smack] I believe called "Maker Schedule, Manager Schedule," where, you know, he said something that all of us have thought before, but he put it very succinctly and in great words.

   3. MSMichael Seibel0:58

      Yes.

   4. DCDalton Caldwell0:58

      And so if you haven't read it before, anyone out there on the internet, um, you should read it. Just Google "Maker Schedule, Manager Schedule." We can put a link in. And he introduces the idea of the difference between how makers, i.e. programmers in his case, organize their time to be productive versus folks that are managers. All right?

   5. MSMichael Seibel1:14

      Business folks.

   6. DCDalton Caldwell1:14

      And so it's great terminology. It's good stuff.

   7. MSMichael Seibel1:16

      Yes. So

3. 1:18 – 3:59

   Maker Schedule

   1. MSMichael Seibel1:18

      let's start with the maker mode. You were a developer in your startup. I was a business guy in my startup. I think, in many ways, this stuff came a little bit more, um, natively to you, and I had to learn this stuff by like basically destroying the productivity of my co-founders. So w- how did you think about maker's mode as a founder?

   2. DCDalton Caldwell1:39

      Most companies are set up around a manager schedule, where you have a day packed with meeting after meeting. And so if you're a programmer at a big company, you would have to... You know, you'd have like an hour to program here and an hour to program there, and this is bad. [laughs]

   3. MSMichael Seibel1:57

      [laughs]

   4. DCDalton Caldwell1:58

      This was not conducive to, to building things, okay? And so to just walk through my perspective as someone that, you know, was programming back in the day when I w- when I was a startup founder. Um, when you're programming, the more of the program you can keep in your head at any one time, the, the easier it is for you to know what's going on and have the context up here to make changes and fix bugs. And it takes like an hour or two cold of looking at a program and figuring stuff out for it to get loaded into RAM, so to speak.

   5. MSMichael Seibel2:31

      Mm-hmm.

   6. DCDalton Caldwell2:31

      And so if you're interrupted, like if you have to program in hour increments, man, are you gonna suck. [laughs] Like, you constantly have to restart your state every time you program. And so a great maker's schedule is something like an eight-hour uninterrupted block of time. And his argument... I think he was also talking about this from the perspective of an artist or a musician, like if you wanted to record an album-

   7. MSMichael Seibel2:56

      Mm-hmm, mm-hmm

   8. DCDalton Caldwell2:56

      ... or write music or if you wanted to write a book. The same deal. If you had to write a book in 20-minute increments, I think a lot of writers wouldn't love that. [laughs] Fair?

   9. MSMichael Seibel3:05

      Which is so much different than the business guy. Like I... You know, I was the business guy at my startup, and you certainly can do email in 20-minute increments or hour increments. And so I remember having this conversation with Emmett where he said, "Michael, imagine that I'm doing ridiculously complicated word problems, and you're interrupting me in the middle of them." And I was like... Then it clicked. I was like, "Oh, well, I've had to do hard word prob-" Like, [laughs] like, I went to school. I had to do that. "Shit, that's what your day's like? Oh." [laughs] One, that sounds a lot harder than writing emails, but two, I would hate to be interrupted like that. And n- and once he said that, it kinda clicked. Um, before he said that, I just assumed, "Well, you know, he's typing. I'm typing."

   10. DCDalton Caldwell3:52

       Yeah, he's typing things. [laughs]

   11. MSMichael Seibel3:55

       [laughs]

   12. DCDalton Caldwell3:55

       And, and I remember, I remember when I read the post, what resonated with me is I felt

4. 3:59 – 5:01

   The Right Time

   1. DCDalton Caldwell3:59

      like my workday really began around 5:00 or 6:00 PM. Isn't that weird? And that's because what... That's when things would quiet down, and I would stop getting email, and the building I was working out of would quiet down, and that's where actually all the good programming happened, was at the end of the day.

   2. MSMichael Seibel4:14

      Wow. What was, what was interesting was that for us, we basically had to figure out how to build that in. I think in the beginning, organically it happened because, you know, that was our sleep cycle. We were all living in an apartment together. But when we had more employees and we had an office, you know, we literally... And this is something that I just noticed happened organically. Nothing got done before lunch. Like getting to work was all about like getting in, answering your email, doing a couple meeting. Like it was just like no one who was writing code even wanted to start writing code before lunch 'cause lunch was the big like F you in the middle of the day. And our whole trick was, one, how do we not serve a lunch that makes everyone go to sleep?

   3. DCDalton Caldwell4:54

      [laughs]

   4. MSMichael Seibel4:54

      And two, how do we make that post-lunchtime free of everything? PG

5. 5:01 – 5:59

   Structure of YC

   1. MSMichael Seibel5:01

      in some ways designed YC a little bit that way, right? I think that's, uh, counterintuitive to a lot of founders. Like, one, there aren't that many events. You don't have classes all day at YC. Like, you know, we try to take as little time as possible during your week so you can actually get shit done. Two, there's a hard deadline, Demo Day. And three, I think people are often surprised, like a good portion of YC is just asking you, "What are you gonna accomplish by Demo Day?" And then asking you every week, "Well, did you do it?"

   2. DCDalton Caldwell5:32

      Yep.

   3. MSMichael Seibel5:33

      And it's you confronting the yes or no of that. [laughs] Like it turns out that like there's a lot of magic around that, and he wanted to build as much maker time as possible in the program. I think in this kind of balance between maker mode and manager mode, what people should be trying to do is maximize their productivity when they're in that mode, right? Ma- how do you maximize productivity? So when I think about manager

6. 5:59 – 6:36

   Manager Schedule

   1. MSMichael Seibel5:59

      mode, for me, I always like to think about this like- Okay, if I'm gonna be managing my time between my to-do list, which is just another way of saying shit that's actually important to get done, [laughs] meetings, email, and Slack, I always think that my to-do list comes first. Like, whenever I'm being productive, I start at the to-do list, and I do everything there, and then I check those things. Whenever I'm being-

   2. DCDalton Caldwell6:25

      Well, 'cause you control it

   3. MSMichael Seibel6:27

      Yes.

   4. DCDalton Caldwell6:27

      Versus-

   5. MSMichael Seibel6:28

      Because I control-

   6. DCDalton Caldwell6:28

      ... if it's inbox-driven, other people are in control of your time, which is, watch out

   7. MSMichael Seibel6:33

      Horrible. Horrible. The

7. 6:36 – 7:38

   Meetings

   1. MSMichael Seibel6:36

      second thing is around meetings, and, like, we talk about this a lot. Like, you're gonna have to have some meetings. Um, I've seen a couple tricks, but they can all be reduced down to write shit down. The worst thing-

   2. DCDalton Caldwell6:49

      [laughs]

   3. MSMichael Seibel6:50

      ... is when you have to have another meeting 'cause people didn't write the shit down [laughs] from the first meeting. Like, like that is, like, when you know you've punched yourself in the face. [laughs]

   4. DCDalton Caldwell7:02

      Right.

   5. MSMichael Seibel7:02

      But like, I'm so shocked. It's like, "No, I'm smart."

   6. DCDalton Caldwell7:04

      And again, let me push you on that 'cause you and I agree. But let me, let me-

   7. MSMichael Seibel7:06

      [laughs]

   8. DCDalton Caldwell7:06

      ... let's make this clear to the audience. What are we saying?

   9. MSMichael Seibel7:08

      Yeah.

   10. DCDalton Caldwell7:08

       What we mean is, say you and I are in a meeting and we agree on something. If neither of us writes it down-

   11. MSMichael Seibel7:13

       [laughs]

   12. DCDalton Caldwell7:13

       ... it's like it never happened.

   13. MSMichael Seibel7:14

       Never.

   14. DCDalton Caldwell7:15

       It's like, uh, we just, we, we were, like, patting ourselves on the back. "What a great meeting, right, Michael?" No one writes it down. We're like, "What did we talk about?"

   15. MSMichael Seibel7:23

       Even if I didn't think I needed it, oh, let's write down the agenda. Oh, let's write our notes what we decided. Ugh, it, that would be great. Any other things that have made you productive as a manager?

   16. DCDalton Caldwell7:35

       The number one thing that I do that I realize

8. 7:38 – 9:38

   Visible KPIs

   1. DCDalton Caldwell7:38

      that a lot of the other successful founders did, too, um, was I had my analytics dashboard or whatever was important KPIs on the business up on my screen-

   2. MSMichael Seibel7:47

      Yes

   3. DCDalton Caldwell7:47

      ... 24/7, and I would stare-

   4. MSMichael Seibel7:48

      Yes

   5. DCDalton Caldwell7:48

      ... at it all the time.

   6. MSMichael Seibel7:50

      Yes.

   7. DCDalton Caldwell7:50

      And I actually can memorize.

   8. MSMichael Seibel7:52

      Yes.

   9. DCDalton Caldwell7:52

      I even... This is even the case for YC, man. I don't even know if you know this, but, like, a lot of our internal stats, I have memorized.

   10. MSMichael Seibel7:59

       Yes. It's-

   11. DCDalton Caldwell8:00

       And it's because I stare at them all the time, and no one told me to do that. This is just-

   12. MSMichael Seibel8:03

       Yes

   13. DCDalton Caldwell8:03

       ... a me thing. But I'm like-

   14. MSMichael Seibel8:05

       I think-

   15. DCDalton Caldwell8:06

       ... obsessed with, like, the internal key KPIs for anything I'm working on. I'm just, like, an addict to look at that stuff, you know?

   16. MSMichael Seibel8:14

       I think that that is such... What we see on the other side, and I completely agree with you, that was a huge thing. Especially for my second start, that was a really huge thing. It's funny, uh, when you talk to a founder who knows their stats well, they just talk about their stats so differently. You know, like, man, like, first of all, they don't round off numbers to the zer- nearest, like, zero, you know? Like, but second of all, they know whether they're up or down 10%, uh, like, at any given time. Like, at any-

   17. DCDalton Caldwell8:42

       Yeah

   18. MSMichael Seibel8:42

       ... given time. Whereas other founders, it's like, "Yeah, I think it was an up week, but..." And it's like, how do you not know? [laughs] It's like how do you not know if your revenue-

   19. DCDalton Caldwell8:51

       [laughs]

   20. MSMichael Seibel8:51

       ... did, like, went up this week? Like, how do you not know that? [laughs]

   21. DCDalton Caldwell8:54

       What are you, what are you doing? Yeah. No, I, I don't get it.

   22. MSMichael Seibel8:57

       [laughs]

   23. DCDalton Caldwell8:57

       I don't get when someone is, like, operating a business, and it's like, "What was our... Do we... What was our revenue last month?"

   24. MSMichael Seibel9:04

       But, but like-

   25. DCDalton Caldwell9:04

       I'll give that to you

   26. MSMichael Seibel9:05

       ... the bookkeeper, they, they give that to me-

   27. DCDalton Caldwell9:06

       [laughs]

   28. MSMichael Seibel9:06

       ... at the end of the month. And it's like, what? Like... Or people didn't know, I mean, for us it was, you know, DAUs, and it was, like, amount of video watched. But it's like everyone on the founding team knew when we had less traffic today than yesterday. Everyone, right?

   29. DCDalton Caldwell9:24

       Yeah.

   30. MSMichael Seibel9:25

       Like, just, just, like, in, like, in their bones. Like, ugh.
9. 9:38 – 10:51

   Your Main Focus

   1. DCDalton Caldwell9:38

      is that the Maker Schedule vibe works for sales and talking to customers, too.

   2. MSMichael Seibel9:43

      Yes.

   3. DCDalton Caldwell9:43

      And that scheduling 20-minute blocks to talk to customers is not the same as an eight-hour... Like, like, even if it's not literally you're a programmer, using the Maker's concept to apply to the things that are the main event of your startup at any one time, and for many folks, that is sales.

   4. MSMichael Seibel10:00

      Yes.

   5. DCDalton Caldwell10:00

      Yeah, you should be scheduling eight-hour blocks. Like, if your, if your, if your job as the co-founder is to be doing sales, and it's, like, a couple of slivers in between other things on your schedule, I don't think that's gonna go well.

   6. MSMichael Seibel10:13

      You know-

   7. DCDalton Caldwell10:13

      Right?

   8. MSMichael Seibel10:14

      ... it's interesting. I agree with you. It's basically this idea of get all of this stupid crap so productive that you can clear out, that every founder can clear out a chunk of their time for the Maker Schedule. And, like, some founders are gonna have to do more of this non-development blocking, tackling. Others are gonna have to do less of it. But I completely agree with you. Like, it's really hard to get anything at a high level done in 20-minute blocks. L- let's talk, though, about the opposite of all these things, right?

   9. DCDalton Caldwell10:42

      [laughs]

   10. MSMichael Seibel10:44

       So, you know, the premise of this chat is how future billionaires get shit done. Let's talk about what we

10. 10:51 – 11:01

    Great founders not do 👇

    1. MSMichael Seibel10:51

       see great founders not do. W- w- what, what comes to mind, f- uh, Dalton? What are founders-

    2. DCDalton Caldwell10:57

       Yeah

    3. MSMichael Seibel10:57

       ... avoiding?

    4. DCDalton Caldwell10:58

       Look, I think the trickiest thing for everybody

11. 11:01 – 13:33

    Social Media

    1. DCDalton Caldwell11:02

       is social media. It's like, uh, social media is the black hole for time.

    2. MSMichael Seibel11:07

       Yes.

    3. DCDalton Caldwell11:07

       And you know, we're all guilty of it, too. Like, it's addictive. And so what's tricky is how to have a healthy relationship with social media-

    4. MSMichael Seibel11:16

       Yep

    5. DCDalton Caldwell11:17

       ... so that you aren't spending 24/7 paying attention to who the main character on Twitter is that said something dumb, and everyone's, like, making fun of him. It's so hard not to do that constantly, and it's also not hard to think that, like, you are a startup founder, and you're succeeding, and you, like, did well. But if I actually, if, like, a, like, a hidden camera was f- shadowing you through the day, it was like you just read Twitter all day. [laughs]

    6. MSMichael Seibel11:43

       [laughs]

    7. DCDalton Caldwell11:43

       You know what I'm saying? Like, imagine if there was, like, a hidden camera auditing what people actually did with a lot of their time.

    8. MSMichael Seibel11:49

       That's it.

    9. DCDalton Caldwell11:49

       I think some people out there would be pretty embarrassed if there was a full, clear-eyed accounting of where their time went. It's like, okay, Discord here, um, TechCrunch here, Twitter here. You know?

    10. MSMichael Seibel12:01

        Yeah.

    11. DCDalton Caldwell12:01

        It's like how much time are you actually spending on not those things?

    12. MSMichael Seibel12:05

        You know-

    13. DCDalton Caldwell12:05

        It's hard, man

    14. MSMichael Seibel12:06

        ... I had a Twitter problem, and, you know, one of the things that I realized is that sometimes willpower isn't enough. You know, like what I did was I follow- unfollowed everyone on Twitter, and then I installed this like Chrome app that basically disables like three-quarters of Twitter's features. And I was just, you know, it was like, "This is an addictive thing. I need a intervention." And that did it. Like that kinda killed my Twitter 'cause it was just like, "Oh, well..." And it was funny 'cause for a while Twitter kept on trying to feed me interesting articles and interesting stuff, but it wasn't... They couldn't really do it because I was not following anyone, I wasn't really interacting with many tweets, and so eventually just like it, it broke. But-

    15. DCDalton Caldwell12:51

        Yeah, I mean, I, I uninstalled Facebook years ago, so I don't have it-

    16. MSMichael Seibel12:55

        Yes

    17. DCDalton Caldwell12:55

        ... I don't have notification turns on. I don't have the Twitter app installed on my phone.

    18. MSMichael Seibel12:58

        Yep, yep.

    19. DCDalton Caldwell12:59

        So again, like ev- everyone should do what works for them, but y- I'm... People that actually are super productive do abnormal things to turn all this crap off.

    20. MSMichael Seibel13:11

        Yeah.

    21. DCDalton Caldwell13:11

        Isn't that... Like you have to like-

    22. MSMichael Seibel13:12

        Yes

    23. DCDalton Caldwell13:13

        ... aggressively be abnormal [laughs] on protecting your time.

    24. MSMichael Seibel13:17

        Yes.

    25. DCDalton Caldwell13:18

        'Cause if you don't, the world is gonna steal your time from you. It's gonna steal your energy from you, and like that's a bad trade-off if you're a startup founder, man.

    26. MSMichael Seibel13:29

        Yeah.

    27. DCDalton Caldwell13:29

        What a waste of time.

    28. MSMichael Seibel13:31

        You know, it's funny. It's like,

12. 13:33 – 14:10

    Tools for Time

    1. MSMichael Seibel13:33

       it's almost like there are these two sets of tools. There's one set of tools that allow you to organize your time better, and there's another set of tools that protect your time, and yeah, effective people use both constantly. And I think ineffective people sometimes are mistaken, and they think, "If I were just had a stronger will, I'd..." Like needing tools is the problem. Like successful people are just have a stronger will, and that's like not true. It's like, no, successful people reach for tools all the time. Like successful people recognize their weaknesses and actually reach for tools. Now, here's something that

13. 14:10 – 16:00

    Startup Mentorship

    1. MSMichael Seibel14:10

       comes up a lot, the collecting of mentors, advisors, weird credentials like advice. "Oh, I went through three different accelerators and an idea lab. Oh, my advisory board. I'm building my advisory board." Why do you think founders are attracted to that versus just building something and launching it?

    2. DCDalton Caldwell14:31

       It smells like you're doing s- successful startup stuff. You're like part of a, the community of startup this, and you know, like there's all this stuff you can do. And I'm not saying like it's all bad, but it, it's, it's a bottomless pit of time suck. Like you could go so far deep in there. You could be in that bottomless pit for years and be a startup founder that's never built a product and has never gotten a single customer because you just cycled in and out of various forms of startup mentorship. It's weird. It's, it's like going to Hollywood and getting acting lessons.

    3. MSMichael Seibel15:04

       Yes.

    4. DCDalton Caldwell15:04

       And like you just... You, you're in like this acting lessons mode for like years, and you're like, "Yeah, I'm an actor." And it's like, you know what I'm saying? Like it feels like you're making progress, right?

    5. MSMichael Seibel15:15

       But you're not. You know, I think a lot of it also has to do with founders being a little bit afraid and thinking these things de-risk. "Well, if I have an advisory board, it's gonna de-risk my startup. It's a bunch of smart people saying my idea is good," or, "If I do a bunch of mentorship, it de-risks my startup. I get a lot of advice." And I don't know. The thing we keep on saying over and over again is like the two things that re- ridiculously redis- re- de-risk your startup, three things, and we'll, we'll get to the third and the second. First one's talking to your customers. The second one's building and launching product. [laughs] Like, and it's like God forbid you're doing anything more than you're doing those things, you are not taking the optimal de-risk strategy. [laughs] Like, um, and then the last one, we see a lot of people trying to hedge their bets.

14. 16:00 – 20:26

    Hedging Bets

    1. MSMichael Seibel16:01

       So many people are trying to be like, "Well, I'm keeping grad school open. I've got a Google job offer. I've got a Jane Street or whatever the new tech finance thing of the minute is, and I'm talking to three friends about doing a startup. And like I'm kind of moving all those pieces down the board at the same time." [laughs] And like we get asked questions like, "Okay, so how do I optimize this?" I'm like, "I don't, I don't think you can be great at those four things at the same time." [laughs] Like it's hard enough to be great at one of those things. [laughs] But like once again, like why should I he- like why shouldn't I hedge, Dalton? Like isn't the optimal move to hedge? Like how do I know I'm making the right decision?

    2. DCDalton Caldwell16:42

       [sighs] When you're taking a high-risk life decision, a lo- you know, like we said, again, like we said on these, this video series a number of times, you're gonna look stupid, and you're gonna take risk, and there's a chance you're gonna be like, "That was a huge mistake." And you wanna like barter with the universe. You wanna, you wanna be like, "Come on. Can't I, can't I like de-risk this?" Like you wanna think that you can be smarter than the system to somehow give up nothing and have no downside and only have upside. And the more you try to barter-

    3. MSMichael Seibel17:17

       Infinite upside, no downside. [laughs]

    4. DCDalton Caldwell17:18

       Yeah. The more you wanna try to barter with the universe to be like, "Okay, first I'll get a job at Google, then I'll save money, and then I'll do, you know, I'll invest in crypto, and then I'll do..." Like y- you wanna like barter with the universe to have no risk. And I guess like I get where I feel... I get where people are coming from. I just, I'm not sure that's a real thing, and I think it's being more real with yourself is like, "Yeah, I'm taking risks." Like yeah, quitting my job at Google is a risk, and this, I may regret it, but I may not. And but I'm doing this with eyes wide open, and by actually putting my full heart into anything I do, whatever that is, including not quitting my job, that's... How can you have regrets about that, being proud of the work you do? I mean, this is what I tell a lot of folks. I do a lot of office hours with people that are shutting down. I did one today. You know, it's like their final office hours 'cause they're shutting down their startup. But I, I tend to tell people similar stuff, which is like, "Look, if you're proud of the job you did- You know, if you, if you had heart and you gave it your all, and you feel like you learned stuff, then great job.

    5. MSMichael Seibel18:20

       Yeah.

    6. DCDalton Caldwell18:20

       And you should view this as an affirmative experience.

    7. MSMichael Seibel18:23

       You didn't fail at-

    8. DCDalton Caldwell18:23

       And so, like, I'm proud of you, I'm proud of the job you did. I know you had your heart into this thing, and like, we'll get the next one. You know?

    9. MSMichael Seibel18:31

       I think that that message has to be told, because it is rewarding, but founders have to be kind of reminded that they didn't fail. Like, it's not like... Or, or let's just put it this way. It's not like failing a test that, like, a, a basic math test that you just didn't study for. It's like, it's not like that. Like, you tried to do something that so few people in the world are successful at. Failing is not really failing, like, at all. Um, you-

    10. DCDalton Caldwell19:00

        It's like, uh, it's like trying to be a pro athlete. Like, where you're really good in college and you try to go pro, and you, like, make a team, and then you get cut in the first year. Like, that's still pretty awesome.

    11. MSMichael Seibel19:09

        Yeah.

    12. DCDalton Caldwell19:09

        Like [laughs]

    13. MSMichael Seibel19:09

        You still were maybe one of the best thousand people on earth who could play basketball. [laughs] Like...

    14. DCDalton Caldwell19:14

        Yeah. And so it's like, m- you know, again, it would be great if you were number one in the world, but like, people are gonna respect what you did. And you, and if you, if you're p- if you're proud in your heart of the work you did, then you will view this as a positive thing in your life, you know?

    15. MSMichael Seibel19:29

        Yeah. And I always tell the people who are hedging, I always say this, the other side, you know, in our world it's really competitive. And what happens if there's a team that's exactly as competent as you, and they're not hedging? They're always gonna win, you know? They're always gonna beat you. So how much better do you have to be than that team if you're splitting your resources two ways, three ways, four ways? Like... So it's not even a good strategy, even if you were trying to think strategically, unfortunately.

    16. DCDalton Caldwell20:00

        No.

    17. MSMichael Seibel20:01

        Um, so yeah. So there you go. Those are some of the things that future billionaires do to get shit done, and some of the things that they avoid as well. Great chat, Donald.

    18. DCDalton Caldwell20:13

        Sounds good. Thanks, man. [outro music]

Episode duration: 20:26