How Future Billionaires Get Sh*t Done
Michael:

This is Michael Seibel with Dalton Caldwell. Today we're going to talk about how future billionaires get shit done. So Dalton, you were inspired by a PG boast when thinking of this idea, right?

Dalton:

Yeah, Paul Graham wrote this really famous blog post, I believe called Maker's Schedule, Manager's Schedule, where he said something that all of us have 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. 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. And so it was great terminology. It's good stuff.

Michael:

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 makers mode as a founder?

Dalton:

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, to building things. And so to just walk through my perspective as someone that was programming back in the day when I was a started founder.

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. 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. And so if you're interrupted, Like if you have to program in hour increments, man, are you gonna suck. Like you constantly have to restart your state every time you program.

And so a great makers 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. Fair.

Michael:

Which is so much different than the business guy. Like, I was the business guy at my startup and you certainly can do email in 20 minute increments or our 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. Shit. That's what your day is like. One, that sounds a lot harder than writing emails. But two, I would hate to be interrupted. And once he said that, I kind of clicked. Before he said that, I just assumed, well, you know, he's typing, I'm typing.

Dalton:

Yeah, he's typing things. And I remember when I read the post, what resonated with me is I felt like my work day really began around five or six p.m. Isn't that weird? And that's when things would quiet down and I would stop getting email in 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.

Michael:

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 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 of 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 like 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 lunchtime free of everything.

PG in some ways designed YC a little bit that way, right? I think that's kind of tutor 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 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? And just you confronting the yes or no of that. It turns out that 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. 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 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. 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.

Dalton:

Because you control it.

Michael:

Yes.

Dalton:

Versus it's inbox driven. Other people are in control of your time which is watch out.

Michael:

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. I've seen a couple tricks, but they can all be reduced down to write shit down. The worst thing is when you have to have another meeting, because people didn't write the shit down from the first meeting. That is when you know you punched yourself in the face. But I'm so shocked. It's like, no, I'm sorry.

Dalton:

Again, let me push you on that, because you and I agree. But let's make this clear to the audience. What are we saying? What we mean is, say you and I are in a meeting and we agree on something. If neither of us writes it down, it's like it never happened. It's like, we just, 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?

Michael:

Even if I didn't think I needed it. Oh, let's write down the agenda. Well, let's write it and that's what we decided. Oh, 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 can memorize. I think this is even the case for YC men. I didn't even know if you know this, but like a lot of our internal stats, I have memorized. 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, First of all, they don't round off numbers to the nearest zero. But second of all, they know whether they're up or down 10% at any given time. Whereas other founders are just like, yeah, I think it was an up week. And it's like, how do you not know? How do you not know if your revenue went up this week? How do you not know?

Dalton:

What are you doing? Yeah, I don't get it. I don't get when someone is operating a business. And it's like, what was our revenue last month?

Michael:

But the bookkeeper, they give that to me at the end of the month. And it's like, what? Or people didn't know. I mean, for us, it was DAUs and it was amount of video watched. Everyone on the founding team knew when we had less traffic today than yesterday. Everyone, just in their bones.

Dalton:

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 it's scheduling 20 minute blocks to talk to customers is not the same as an eight hour. 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. Yeah, you should be scheduling eight hour blocks. 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 going to go well, right?

Michael:

You know, 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 going to have to do more of this non development blocking, tackling others are going to have to do less of it. ButmI completely agree with you. 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 the premise of this chat is how future billionaires get shit 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 a social media is the black hole for time. 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. It's like, okay, Discord here, TechCrunch here, Twitter here, you know. It's like, how much time are you actually spending on not those things? It's hard, man.

Michael:

I had a Twitter problem. And one of the things that I realized is that sometimes willpower isn't enough. What I did was I unfollowed everyone on Twitter. And then I installed this Chrome app that basically disables three quarters of Twitter's features. And I was just, it was like, this is an addictive thing. I need a intervention. And that did it. Like that kind of 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 broke, but yeah.

Dalton:

I mean, I, I uninstalled Facebook years ago, so I don't have it. I don't have notifications on. I don't have the Twitter app installed on my phone. So again, like everyone should do what works for them, but People that actually are super productive do abnormal things to turn all this crap off. You have to aggressively be abnormal on protecting your time. Because if you don't, the world is gonna steal your time from you. It's gonna steal your energy from you. And that's a bad trade-off if you're a startup founder, man. What a waste of time.

Michael:

You know, it's funny. It's like, 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, 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 someone that comes up a lot. The collecting of mentors, advisors, weird credentials like advice Oh, I went through three different accelerators in an idea lab. Oh, my advisory board. I'm building my advisory board. Why do you think founders are trying to do 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 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. And like you just, you're going to 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?

Michael:

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 that'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 at de-risk 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 ridiculously re-de-risk your startup. Three things. We'll get to the third one in a second. First one's talking to your customers. The second one's building a launching product. 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.

And then the last one, we see a lot of people trying to hedge their bets. 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 I'm kind of moving all those pieces down the board at the same time. And we get asked questions like, okay, so how do I optimize this? I'm like, I don't think you can be great at those four things at the same time. It's hard enough to be great at one of those things. But once again, why shouldn't I hedge? Delta isn't the optimal move to hedge. How do I know I'm making the right decision?

Dalton:

when you're taking a high risk life decision, like we said, again, like we said on this video series, never 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 barter with the universe. You wanna be like, come on, can't I de-risk this? 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 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 it like. You want to like barter with the universe to have no risk and I guess like.

I get where people are coming from. 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 I may regret it, but I may not. 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 didn't one today. You know, it's like their final office hours because they're shutting down their 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 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. 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.

Michael:

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.

Dalton:

It's like a it's like trying to be a pro athlete like where 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

Michael:

Yeah, like one of the best thousand people on earth who could play basketball

Dalton:

Yeah, and so it's like Again, it would be great if you were number one in the world, but people are going to 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.

Michael:

And I always tell the people who are hedging, I always say this the other side. 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. 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? So it's not even a good strategy, even if you were trying to think strategically, unfortunately.

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.