The Decision Register, Newsletter Woes and An Audience of One

So I have this list list of questions that I sell, uh, I have this document that I have, but I call it the decision register, where I basically write down every major decision that I make. And so, for example, the very first one that I have in this list is from when I was 18 years old. It says, quit pre-med. This was, uh, sorry, I was 20, 21 years old. So I'm, I'm, I'm a senior in college, I'm pre-med, I take the MCAT, but I decide not to go to med school.

I'm like, we could Is this the obvious way? But let's try something. Stick out your tongue. I'm gonna, we'll use that for your ACL. All right. So, and then I have an next column that says, did, did it seem big in the moment? 'Cause one learning was a lot of the biggest decisions didn't actually seem big in the moment, uh, but turned out to be an important decision. And then I basically have like kind of the, what was the one decisive reason why? So if I boil down like not a long list of pros and cons, but like what's the one thing that like, The main reason I made that decision and then outcome and lesson learned. And so I'll give you another example. Decision: sell to Twitch and not to Facebook. Those are the two final companies that we had given us good offers and we turned down more money from Facebook to take the Twitch offer. Did it seem big? Yeah, felt big in the moment. Why? Because after 6 years of a startup, I was tired and Facebook was looking at us like we were gonna save their kind of gaming initiative. Uh, you know, they were looking at us to like make that, make it happen where I was like, Twitch has already won. I like, you know, I can just cruise control when I'm here. Like, let me just go play for the winning team versus trying to like take the underdog from the bottom of the league to the top, um, in terms of the, this industry. And, uh, you know, then it's like, you know, one of the lessons learned is, you know, I don't know what the other side was, so I know what I got out of it. So I think it was a good call. I'm happy with the decision, but you never know. And that's how a lot of these decisions go. So I have this decision register. Now, a version of it would be, uh, like there's a bunch of investment decisions here, you know, like not buying Ethereum and Bitcoin when the smartest people I knew literally working in my office were doing it at the time. Didn't seem like a big decision. I just kind of overlooked it. I didn't even realize this was a big decision I was making. Seemed weird. I just kind of laughed at something because it seemed strange rather than leaning in and trying to understand why, why are you so excited about this? And like, hmm, could I place a small tester bet? Right? So terrible decision, bad call. You know, and I didn't pay attention to a signal, which is what the nerds do on the weekend. We'll probably all do, you know, in a few years. And this is what the nerds were doing on the weekend back then. They were really interested in cryptocurrencies. Okay, so anyways, I have this like decision register now with it. I have a bunch of like questions that I ask when I'm gonna make a decision. Let me pull that doc up real quick.

Um, no, I started it like 4 or 5 years ago, but I back I tried to go back and figure out like, and this is like a Google Doc, just a Google Doc. Exactly. And I highly, highly recommend this because again, judgment and decision making is the most important thing you can have. People are terrible at actually honing that. They always say, oh yeah, I learned a lesson. Really? What, what was it? Did you, did you write down what you were thinking then and what you've learned since? No. Like, you know, we put very little effort into this and so I, I, I've I basically realized one edge, one source of alpha is to take a disproportionate amount of time than most people. It doesn't even take that much time, right? It's like, you know, couple hours twice a year. But just doing that exercise can improve my judgment at a rate maybe 2 or 3x what a normal person's would, would, would do. And then all of a sudden people are like, man, uh, you know, how do you, you know, like whatever, where do you get this wisdom from?

All right, so here's the decisions I, here's the questions I ask for an investment. Here's what I have to run through. I say, what is the decision? Explain why I'm doing this in a tweet length. So I have to be able to explain why I'm doing the decision in a tweet length. Uh, what alternatives did I consider? Did I consider any alternatives? What am I feeling? And I have some options, uh, like extreme fear, pessimism, neutral, boredom, fatigue, greed, extreme greed, FOMO, right? Like those, those are things I could be feeling right now. Uh, how long have I been thinking about this decision? Right? Is it a few hours, few days, few weeks, few months, few years? Who and what tipped me over the edge? So what is like kind of the last conversation or podcast or thing I read that like made me make, take action? What are the secondary benefits of this? So like, can I sleep better at night because I'm not worried about a margin call or something like that? If I took away all the secondary benefits, would I still make this decision? Yes or no? What makes me think I'm right? So I have to write, why do I think I'm right about this? What makes me, what makes you think I might be wrong? Upside if I'm right, downside if I'm wrong. So I have to define those two. And I say, what follow-up decision should I make to make this decision more successful? And then how do you predict that this is gonna play out? And I have to like answer how I predict it's gonna play out. And then I basically set a date. It says, what date will you revisit this? And so I'll go revisit this. Um, and so I did this for when I sold all my stocks. So I could go look at this right now and be like, Was I right? Was I wrong? Do I— what can I learn from how I was thinking then so that the next time I can think better basically about this?

This is just smallboy.co. Uh, yeah, dude, that thing's grown like crazy, man. We have like 100,000 people on the list now and, uh, it's amazing. That's like in a very short period of, short period of time.

You ignore them. I've learned to ignore them because my friend Ramin has this great little framework he says, which is that every business is hard. It's just hard in one of two places. It's either hard 0 to 1 or it's hard 1 to end. And what he means by that is like, it's some businesses are really hard to get started and get initial momentum. And then some businesses are really hard, like really easy to get initial momentum, But then turning that into a valuable business that's like at scale is really hard. And I would say because of this podcast, people basically see Sam did it with newsletter, Sean did it with the newsletter. I too will do, you know, the AI version of this. Like, you know, I'll do the whatever version of this. Newsletters are very easy 0-to-1 businesses. They're not easy 1-to-N. And as I've talked to people that are doing this and they're asking for kind of advice or whatever, I'm like, talk to me in 6 months. I told one of the AI guys straight up, I go, you're gonna drive— this is driving off a cliff. You don't even realize it yet. And I was like, he's like, why? And I was like, you know, to explain this to you will take like, you know, some time and like explain what, what I think you should do instead. I don't really feel like coaching that, but I'm just gonna tell you like, please don't fall in love with this as is because I'm telling you that this isn't, this isn't gonna work. This is not the answer to making something that's successful. Like, because it's very easy to see just the subscriber count going up. Or like if you're in a hot space like AI, you'll get easy sponsorship revenue for like, you know, the next 6 to 12 months. But like if you want to take this to the finish line where this thing is spitting off millions of dollars a year profit and you're able to sell it for maybe tens of millions of dollars, which is what all these people I think would dream of doing, that's where the real skill comes in in this. And I think that a lot of these people, I do not feel are equipped to do that based on what I hear their plans are.

The person who's done it best, I think, is Austin Rief for Morning Brew. It's 10 years old now. I think they publicly said that revenue is in the $70 to $90 range. I forget exactly what they said publicly, but something like that. 200, 250 employees. I forget. I went to their office, dude. He's got like a tech office setup. It's like a beautiful office. Like, he has done it all the right way where, I mean, he's made a bunch of errors just like everyone, but that they, he's done such a good job of having durability and long-term view and also short-term, like moving quickly. That guy's a machine. He's one of the more impressive operators.

yeah, they're challenging. What they don't see is that Morning Brew at this point, the hustle I don't know how many employees they have now, but we don't sell ads. But with Morning Brew, in order to make $70 or $80 million a year in revenue, you need 80 salespeople. And if you have 80 salespeople, you also need 30, like, people to, like, handle the stuff that they're selling.

You also need, like, evergreen content. Like, you guys talk about what's going on in general with general business. People who are doing these AI newsletters right now, they're like, Here's the latest new demo in AI. Guess what? 18 months from now, that shit's not gonna be interesting at all to anybody. And the advertisers are gonna realize that the type of person who just wants to like see an AI demo is not very valuable to advertise to. Milk Road worked because people who read about crypto, like what's going on in crypto, were crypto investors. Crypto investors are a very valuable audience segment. And that, and so that was very different than just like, so Crypto, AI, they're all just topics, right? They're all just the new thing. No, no, no. Because the people who read about crypto were putting tens of thousands, hundreds of thousands, or millions of dollars into those portfolios and were a very valuable customer. That's not true with an AI reader, right? But they don't see that. They just see the surface level stuff. They're not thinking about it critically enough to realize that they're just riding this like kind of current momentum where every day there's like a mind-blowing demo and people are curious. 18 months from now, that, that's gonna fatigue out. That is not gonna be the case that And then, and also your advertisers are gonna realize that like, cool, advertising to the random guy who likes to see like, you know, the cool stuff that AI could do, that's not translating into a lot of money because that's not a very valuable, uh, audience demo. Um, it's not gonna work.

And you can't be a mercenary about the content. Like a lot of people are like, oh, I just hired this person overseas and we use AI to actually make the content. And, uh, that's really hard. Not impossible, but it's hard. At the end of the day, when you have a newsletter, you have to get someone to act. You have to say, I am going to be at this location at this time. And if no one shows up, then your shit sucks. And getting people to do that is really, really, really hard. It's very challenging. At the end of the day, it's about getting people to take an action, whether it's to buy something, to show up somewhere. And that's really fucking hard if you're a mercenary versus a missionary and you're like all in on this shit. That's why Milk Road worked, because you said I— one of the coolest things you guys did was I invested this much money into crypto. Here's my portfolio. You can see it as we go. I am, I'm in this shit and I'm gonna talk about that.

And the news, and I, I talked about the stuff that like each day it was basically what is the thing I'm most curious about? That was the only guiding principle. It wasn't like news, it wasn't announcements. It like if those were in the letter newsletter, cool, that's fine. But the lead story had to be the thing that I thought was most interesting, which was sometimes Twitter drama, which was sometimes a cool product, which was sometimes a price analysis, which was sometimes whatever. And, um, that's very different than if you hire a journalist or an aggregator to basically like summarize headlines from stuff. And so, you know, that worked for us. I don't think that's the only way to make it work, but, uh, it was one of the ways where it felt very different. And like you said, like if we said, hey, we're going to be here at this time and date, people would cut— people would come because they were excited. Um, and they were excited to meet us. They were excited to meet other people that are like them. And the brand, you know, had, had some influence. On people, which is what you need in order to do this. If you just throw up a quick Beehive newsletter and you get like, you know, 12,000 subscribers, and like, you know, the number of subscribers is really the wrong metric. I guess that's the other way of putting it. People— it's the easiest metric, and again, the easiest metric is not the right metric necessarily. It's the easiest metric to look at, but I don't think it's the right metric to look at for a newsletter.

Yeah. Uh, Sagar and I forgot what her name is. Uh, uh, there's the woman there too. They're, they're good. And so they, uh, and what'd he say? At first he just tries to brush it off. He's like, he's like. I don't know. I don't know. It's kind of like fake humility, but also I think he's trying to make a point, which is it's not some calculated thing. But the guy pushes. He's like, but there must be something, whether you planned it or you intuitively do it. You agree there's a difference between what you're doing and what other people are doing, and there's a difference in the results you're getting. If you had to think about it, if you had to answer, what would you answer? It's kind of pushing him. And he goes, he goes, I think that's the thing. I don't have a, like, I don't come in with this sort of like plan or agenda. He goes, look, when I started this podcast, I didn't think anybody listened. You couldn't even tell if anybody was listening. And he's like, so I just really had nothing to lose and I just decided to do it the way I wanted to do it. So like, I just wanted, like, if I'm chilling with my friends and we're smoking weed and that's what the episode is, great, because that's what I wanted to do. If I'm fascinated by this alien conspiracy and I can talk to this scientist, great, that's the conversation I want to have. Everybody told me like, this needs to be 1 hour long, it needs to be shorter, 3 hours is just too long. He's like, but I didn't like how the conversation was going to be in an hour. I liked having the 3-hour conversation, so that's what I did, even though it like, you know, broke the rule. It wasn't like audience-driven. He goes, and so now he's like, basically That's what was working, so I just decided not to change it. He's like, basically, I just, this podcast is a massive education for me. I have the conversations I want to have in the way that I want to have it. And, um, you know, I just don't do things that are like, lean into this. The audience is really responding to this. He goes, that's how you end up like those late night talk shows where everything is just fake. Like the host is fake, the interactions are fake. It's just like, it's almost like it's quote unquote professional, but it's the least real thing. And he is like, I don't think people like that actually. He goes, podcasts are professionally unprofessional. And he goes, I, he goes, I just don't read the comments and I don't try to do things based on what the ratings and reviews are gonna be. He goes, I realized the only way for this to be interesting was if I'm actually interested in it. I can't, he's like, you can't fake being interested in it for very long. It comes through. He's like, so the only way to do this is if I'm interested in it and then I'm just, the audience will be what it's gonna be at that point. Like it'll just be the other people who are interested in this and that's sustainable. Sustainable for like kind of forever. And I thought that that is, it relates to like Hasan Minhaj. He, he said this thing to me once. He goes, he goes, I'm not, he goes, I'm like, why aren't you on TikTok, bro? Like, why aren't you more on Instagram? Like, you could be killing it, dude. These are growing. I'm giving him all the logical reasons to be on. He goes, I don't want to be on because I know to do that, to win in those games, you just have to dance for the algorithm. Like whatever the algorithm wants, that's what you gotta do. And he's like, I just don't want to do that. I want to be an artist. He goes, the best He's like, I come from comedy and the best people who are the best comedians, they, um, they're free. They just do what they want and they are the judge. They don't care really. Like they pick up on signals from how people react to it, but like they are the end decision maker of if something was good or not. And he is like, you see this in everything. He goes, he goes, I, he goes, I love basketball. You see this on the basketball court, guys like Steph Curry or Luka Dončić. They're free. They're just playing how they wanna play and that's it. They don't, they're not like overthinking it. They don't, they don't, they don't have this like voice in their head that's constantly judging it and thinking it. They're actually free to just create their art. And he is like, that's what he is like, that's like how the best people operate. And, um, Rogan said the same thing about comedians. He goes, if you watch Dave Chappelle, he'll do these shows in front of like 50 people. He's done shows in front of 50,000 people, but he does it in front of 50 people. He's having a great time.

Yeah, yeah, yeah, exactly. And just who, ultimately who's in charge, right? Like you might have 3 co-founders in your business, but ultimately push— who makes the decision if push comes to shove? Obviously you all talk about it, you all have a, a, a say, but if a decision needs to be made, who can, who can make a final call in a tough, tough spot? And I think that's in, on the content side, I think that who makes the tough call in the end has to be, do you think it's good? Do you like it? Are you interested in it?