How Future Billionaires Get Sh*t Done

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 when I tell something to founders and then they write it down in a notebook, I'm like, that's gone forever. But they look cool—they have like a fountain pen and they're like taking beautiful notes.

Michael: We all know that everything important is. This is Michael Seibel with Dalton Caldwell. Today we're going to talk about how future billionaires get things done. So Dalton, you were inspired by a PG post when thinking of this idea, right?

Dalton: Yeah, Paul Graham wrote this really famous blog post, um, I believe called "Maker Schedule, Manager Schedule," where he said something that all of us had thought before but he put it very succinctly and in great words. And so if you haven't read it before, anyone out there on the internet, you should read it. Just Google "Maker Schedule, Manager Schedule." We can put a link in.

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.

Michael: All right, and so it's great terminology; it's good stuff.

Dalton: Yes, so 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 natively to you, and I had to learn this stuff by like basically destroying the productivity of my co-founders. So how did you think about maker mode as a founder?

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, an hour to program there; and this is bad. This was not conducive to building things.

Okay, and so to just walk through my perspective of someone that, you know, was programming back in the day 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 easier it is for you to know what's going on and have the context up here to make changes and fix bugs. 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.

And so if you're interrupted, like if you have to program in hour increments, man, are you going to suck? Like, you constantly have to restart your state every time you program. And so a great maker 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 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.

Michael: Fair, 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 work, like I went to school; I had to do that." That's what your day is like.

One, that sounds a lot harder than writing emails. But two, I would hate to be interrupted like that. And once he said that, it kind of clicked. Before he said that, I just assumed, well, you know, he's typing on typing.

Yeah, he's typing things, and I remember when I read the post, what resonated with me is I felt like my workday really began around five or six p.m. Isn't that weird? And that's because 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.

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, 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 getting in, answering your email, doing a couple meetings. Like, it was just like no one who was writing code even wanted to start writing code before lunch because lunch was the big "FU" 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? And two, how do we make that post-lunch time free of everything?

PG, in some ways, designed YC a little bit that way, right? I think that’s 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 stuff 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 going to accomplish by demo day?" And then asking you every week, "Well, did you do it?"

Yep, and it's you confronting the yes or no of that. Like it turns out that like there's a lot of magic on 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? How do you maximize productivity?

So when I think about manager mode for me, I always like to think about this: like, okay, if I'm going to be managing my time between my to-do list, which is just another way of saying, that's actually important to get done, 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 control it.

Yes, versus if it's inbox driven, other people are in control of your time, which is, watch out, horrible, horrible. The second thing is around meetings, and like we talk about this a lot—like you're going to have to have some meetings.

Um, I've seen a couple tricks, but they can all be reduced down to write down. The worst thing is when you have to have another meeting because people didn't write it down from the first meeting. That is like when you know you've punched yourself in the face.

Michael: But like, I'm so shocked. It's like no one—again, let me push you on that because you and I agree, but let me—let's make this clear for the audience. What are we saying? What we mean is say you and I are in a meeting, we agree on something. If no one writes it down, it's like it never happened. It's like we were like patting ourselves on the back, "What a great meeting," right, Michael? No one writes it down, we're like, "What do we talk about?" Even if I didn't think I needed it—oh, let's write down the agenda. Oh, let's write our notes where we decided—uh, that would be great.

Any other things that have made you productive as a manager?

Dalton: The number one thing that I do that I realize that a lot of the other successful founders did too was I had my analytics dashboard or whatever was important KPIs on the business up on my screen 24/7, and I would stare at it all the time. And I actually could memorize. 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. Yes, and it's because I stare at them all the time, and no one told me to do that; this is just a me thing, but I'm like obsessed with like the internal key KPIs for anything I'm working on. I'm just like an addict to look at that stuff.

Michael: 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 startup. That was a really huge thing. It's funny 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 nearest like zero, you know? Like, but second of all, they know whether they're up or down 10 percent at any given time—like at any given time—whereas other founders, it's like, "Yeah, I think it was an up week." But it's like, how do you not know? How do you not know if your revenue like went up this week? Like what are you—what are you doing?

Dalton: Yeah, no, I—I don't get it. I don't get when someone is like operating a business and it's like, "What was I do? What was our revenue last month?" But like, keeper—they give that to me 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? Like just—just like in like in their bones—like, "Oh, I think my last point on this manager schedule." The thing I would just add is what I've learned that I did not appreciate when I was a founder is that the maker schedule vibe works for sales and talking to customers too. And scheduling 20-minute blocks to talk to customers is not the same as an eight-hour—like even if it's not literally your 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.

Michael: Yes, yeah, you should be scheduling eight-hour blocks. Like if you're—if you're—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. You know?

Dalton: Right, 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's schedule. And like some founders are gonna have to do more of this non-development blocking and 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.

Let's talk though about the opposite of all these things, right? So you know, the premise of this chat is how future billionaires get done. Let's talk about what we see great founders not do. What comes to mind, Dalton? What are founders avoiding?

Dalton: Look, I think the trickiest thing for everybody is social media. It's like social media is the black hole for time. Yes, 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 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 them. 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 hidden camera was shadowing you through the day, it was like you just read Twitter all day. 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.

I think some people out there would be pretty embarrassed if there was a full clear-eyed accounting of where their time went. So okay, Discord here, um, TechCrunch here, Twitter here—you know, it's like how much time are you actually spending on not those things? You know, it's hard, man. 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 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 an intervention. And that did it—like that kind of killed my Twitter because it was just like, "Oh, well." And it was funny because for a while, Twitter kept on trying to feed me interesting articles and interesting stuff, but it was—they couldn't really do it because I was not following anyone; I wasn't really interacting with many tweets.

And so eventually, it just like broke. But yeah, I mean, I uninstalled Facebook years ago, so I don't have it. I don't have notification turns on; I don't have the Twitter app installed on my phone. So again, like everyone should do what works for them, but I'm—people that actually are super productive do abnormal things to turn all this crap off.

Yeah, isn't that like—you have to like aggressively be abnormal on protecting your time?

Dalton: Yes, because if you don't, the world is going to steal your time from you; it's going to steal your energy from you, and like that's a bad trade-off if you're a startup founder, man. Yeah, what a waste of time.

You know, it's funny—it's almost like 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. 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—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 the one that 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?

Dalton: It smells like you're doing successful startup stuff. You're like part of 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'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 like going to Hollywood and getting acting lessons. Yes, and like you just—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? 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 do risk. Well, if I have an advisory board, it's going to 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 really ridiculously de-risk your startup—three things, and we'll get to the third one. The second—first one's talking to your customers; the second one is building and launching a product.

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. Like, um, and then the last one, we see a lot of people trying to hedge their bets. So many people 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.

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. Like it's hard enough to be great at one of those things, but like once again, like why should I have—like why shouldn't I hedge, Dalton? Like isn't the optimal move to hedge? Like how do I know making the right decision when you're taking a high-risk life decision a lot?

You know, like we said again, like we said on these—this video series. Never times you're going to look stupid and you're going to take risks, and there's a chance you're going to be like, "That was a huge mistake." And you want to barter with the universe; you wanna be like, “Come on, can I—can I like do you 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—yeah, the more you want to try to barter with the universe to be like, "Okay, first I'll get a job at Google and I'll save money, and then I'll do, you know, I'll invest in crypto, and then I'll do like"—you want to 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 of people that are shutting down. I did one today, you know, it's like their final office hours because they're showing another startup.

But 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 a heart and you gave it your all and you feel like you learned stuff, then great job, and you should view this as an affirmative experience. You didn't—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?

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 let's just put it this way; it's not like failing a test, that like 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; it's like it's like trying to be a pro athlete.

Like you're really good in college; 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. You still were really one of the best thousand people on earth who could play basketball.

Yeah, and so it's like, 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 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?

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 going to win, you know? They're always going to 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.

No, um, so yeah, so there you go. Those are some of the things that future billionaires do to get done and some of the things that they avoid as well.

Michael: Great chat, sounds good. Thanks, man.