The Decision Register, Newsletter Woes and An Audience of One

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 I learned a lesson. Really? What? What was it? Did you r did you write down what you were thinking then and what you've learned since? No. Like you know, you we put very little effort into this. I feel like I can rule the world, I know I could be what I want to I put my all in it like a day's all on a roll, less travel, never left. So I have this 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 is from when I was eighteen years old. It says quit pre med. This is uh sorry, maybe I was twenty twenty one years old. So I'm I'm at s I'm a senior in college, I'm pre med. I take the MCAS, but I decide not to go to med school. The most obvious obviously good decision you've ever made. So I then I have the here's the call. You'd be the worst doctor. I'm like we could fix this the obvious way, but let's try something. Stick out your tongue. We'll use that for your ACL.

And then I have an ex call and says, D 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 ha we had had given us Good offers and we turn down more money from Facebook to take the Twitch offer. Did it seem big? Yeah, felt big in the moment. Why? Because after six 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 the make it happen. Where I was like, Twitch has already won. Oh, like I you know, I can just cruise control when I'm here. Like let me just go play for the winning team versus try 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, but 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 registered. Now A version of it would be uh like there's a bunch of investment decisions here, you know, like not buy Ethereum and Bitcoin when The smartest people I knew. Literally working in my office, we're 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 are you so excited about this? And like,

Hm. Could I place a small test or bet, right? So terrible decision, bad call. Um 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.

And you've been is this a running document that you've had for ten years? Uh no. I started it Like four or five years ago, but I back I tried to go back and figure out like And it's 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 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, you we put very little effort into this. And so I I've I've I r 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, w couple hours. Twice a year. Just doing that exercise can improve my judgment at a rate maybe two or three X 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 I Like whatever. Where do you get this wisdom from? Sean, you're so good at you're you're so wise. Yeah, you're such a good at decision making. 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, a 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 make me what makes me think I might be wrong? Upside if I'm right.

Downside if I'm wrong, so I have to define those two. 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 can basically set a date and 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 stock. So I could go look at this right now and be like Was I right? Was I wrong. Do I d what can I learn from how I was thinking then so that the next time I can Think better basically about this. Like how many decisions do you have that you've documented this way? I think I have done this maybe four or five times now in the last like, you know, two, three years. Yeah, like selling a milk was one, for example.

You know, making a big financial decision, m investing in um you know, a private company. You know, deciding to rent instead of buy a house right now. Things like that. Do you consult your wife when you do these things as well? No, I probably should. She she wishes I did, but I

Don't Well not necessarily like asking for permission, but like getting your her perspective. Yeah, that's the problem. I want her perspective, but I feel like uh the there's like the the the messed up psychology in me is like kinda turns into asking for permission at some point. You know, like you gotta be a line to do this. And like what if she's not a line? Uh maybe I'll just do this, which she hates. And how much decision or how much like When you're selling the milk road. Yeah. You sold the last company, I think, before you were married.

But when you're selling the milk road Are you like, Hey, just so you know, this is happening. Or is it like Hey, it's happened. No, no. I talked to her a bunch. I got her opinion on it uh you know several times during the process. And uh you know, she she's very helpful with that. It's more of the like stock or startup investments that I don't really remember because I'm like Man, I'll have to explain so much context because it's not an area she pays attention to. She doesn't pay attention to the stock market. She's never bought a stock in her life.

She doesn't know about startup investing, angel investing, or these companies. So I'm like, oh man, the context for that is really hard, but like selling a decision to sell a company or buy a company. That's much easier to explain. Right. No, I I consult my wife a ton on this stuff.

But I I th I think it's more so of like I just need to speak this and like I need you to just like be a brainstorming partner. Sarah's up a little bit like that character on billions, the like the office Like uh Wendy. Yeah, w like mindset coach or a psychologist or whatever. I feel like she's like Wendy. Like her demeanor is like so even keel. Like I can see her being like, I'm gonna help you with this decision versus like this is our decision, I'm gonna have my opinion, you're gonna have your opinion, then we're gonna figure out whose opinion is right. Totally.

Yes, and I think that I have a history of making emotional decisions and so I I'm a lot of times I need someone to just be like Hey, don't be crazy. Don't do this right now. Just like sleep on it. Just wait. Just wait.

Um Dude, the decision register is good. I think you should I think you're a very talented at these frameworks. I'm gonna probably steal that for Hampton, because I think it's quite good. So you have to post it on the YouTube link. So yeah I can actually read it. I do something similar, it's different. This is more organized. I'll put it I'll put a link to it in the description on the show notes for YouTube and whatever, and you can just I'll just make it a template, people can make a copy of it for themselves.

Um And that's on we'll we'll plug your thing, small boy. Is it dot co or dot com? Daco, yeah. A b a boy spelled normal or like baller boy. Not B O I no Normal Boy. Small normal. Smallboy.co. Uh yeah, dude. That thing's grown like crazy, man. We have like a hundred thousand people on the list now. And uh

It's amazing. That's like in a very short a period short period of time. Did you start at zero? I started at for uh forty K thirty eight K, I think. When did you start it? So I had thirty eight K from like Yeah, old email newsletter, five three Tuesday type of thing. And then Basically at the

start of this year ish, like maybe February or something. Six months ago. Yeah, maybe five, six months ago started. Any paid marketing? Uh yeah, paid marketing on um Uh a little bit of paid marketing. Uh you know, still I think half is like organic or something like that. So, you know, it's like half organic growth, half paid growth.

Dude. Newsletters, man. They're the best. The best I take all the credit. I take a hundred percent of the credit. I get one h not your effort, not your day to day hard work.

It's all me of just saying. Newsletters are cool. Exactly. Um I'll take that I'll take one hundred newsletters are awesome. Dude, my d my decision register for why to start the milk road was like I think I know how to do this'cause I watched Sam do this like from scratch with the hustle and like I think if you took the hustle plus crypto. That would work.

That was like, you know, the whole thing. Pretty sure Hustle Plus Crypto would work. Secondary benefits. Like just do in the hustle plus the or or as you say it. It's like You're like the milk road of

Business in tech news. Uh you know, th what's the hustle? It's like the milk road but for this thing. But no, the milk road, the hustle plus anything, it's it's all that will work. For the foreseeable future, I think. Well, you know what's funny, I don't know how much you get hit up by these people who are doing newsletter businesses, probably all the time.

I ignore them. You ignore'em. I've learned to ignore'em because My friend Ramin has this great little framework he says, which is the every business is hard. It's just hard in one of two places. It's either hard zero to one or it's hard one to end. And what he means by that is like it's some business 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, um, 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 zero to one businesses. They're not easy one to end. And as I've talked to people that are doing this and they're asking for kind of advice or whatever. I might Talk to me in six months. I told one of the AI guys straight up, I go

You're gonna drive this is driving off a cliff and 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 the this isn't going to 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 s sponsorship revenue for like, you know, the next six to twelve months.

But like if you want to take this to the finish line where this thing is spitting off millions of dollars a year of 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's 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 Reef.

For morning. It's ten years old now. I think they publicly said that revenue is in the seventy to ninety range. I forget exactly what they said publicly, but something like that. Two hundred. Two hundred and fifty employees, I forget. I went to their office.

Dude. He's got like a tech office set up. 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. Well the thing is people see that, they see the hustle, um, and they see just like the tip of the iceberg, right? It's like this iceberg theory, like

When you see an iceberg in the water, you're only seeing, you know, the top little bit. You don't see the giant ninety percent of the mass is under the water. The benefit for me with Milk Road was I was there when you We're doing just events and then blogs and then you pivoted to the newsletter. We were in a mastermind group, so we're checking in every month. Every month we would meet, we would talk about what's going on.

What you're trying to do And so I got to see s the five year Under the water. Like build up.

And I think I'm not going to be able to most people don't have that like that's a that's just luck basically for me that I had that And that's why Milk Road was able to work a lot better than if I hadn't had that. Most people don't have that. They're just trying to copy what they see on the surface level. And that'll get you kind of the zero to one. I don't know if that's gonna get you the one to N. I

I think for most people not. I think if you're a great entrepreneur, you'll make it work no matter what. Uh the problem is You survey ten entrepreneurs, they all think they're a great entrepreneur, but sort of by definition, not everybody's above average, right? Like you can maybe one out of the ten are. The problem is all all ten think that they're that one. And uh, you know, that's gonna be. Yeah, they're they're challenging. What they don't see is that morning brew at this point. I I don't know how many employees they have now, but they we don't sell ads. But with Morning Brew, in order to make seventy or eighty million dollars a year in revenue, you need Eighty salespeople.

And if you have eighty salespeople, you also need thirty 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? Eighteen months from now, that shit's not gonna be interesting. At all. To anybody. And the advertisers are going to 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. They 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 write about crypto We're putting tens of thousands, hundreds of thousands, or millions of dollars into those portfolios, and we're 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 writing this like kind of current momentum where Every day there's like a mind blowing demo and people are

Curious. eighteen months from now, that f 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 c 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 gonna 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 Yeah, I'm in this shit. And I'm gonna talk about that and then 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. 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 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 a a a journalist or or an aggregator to basically like summarize headlines from stuff.

And so you know, that works 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 gonna be here at this time and they People would cut. People would come'cause they were excited. Um, and they were excited to meet us. They were excited to 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

Behive newsletter. And you get like you know twelve thousand 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 the 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. This is one of those episodes where We talked about stuff that I personally care about. I could talk about this newsletter crap forever. I could talk about personal finances forever.

This rate it might be a high ratio of things we love to talk about. But maybe our audience doesn't all entirely love, but I'm very eager to see the response to this. I could talk about this stuff forever. And by the way. I think that's the only way this podcast can work. is uh like it's I was watching this thing uh uh Joe Rogan. Joe Rogan doesn't go on very many other podcasts.

But one of the ones he goes on is like this breaking points news thing that he likes. So they interviewed him. And they go. Joe, what uh you know, like everybody does podcast everybody does interviews. Not everybody's having like What's your the like what you what you've created with JRE like what are you doing differently?

Breaking points is awesome. Yeah. I know breaking points, yeah. Uh Sagar and I I forgot what her name is, uh the woman there that too. They're they're good. And so they uh And what do you say? At first he just tries to brush off. He's he's like I don't know. I don't like I don't know. It's like kinda like fake humility, but also like he think he's trying to make a point, which is it's not some calculated thing.

And then the g but the guy pushes, he's like But there must be something. Like Whether you n whether you planned it. Or you intuitively do it y like 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. Like

Just w if you had to think about it, w if you had to answer, what would you answer? 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 wanna like if I'm chilling with my friends and we're smoking weed and that's the 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 one hour long, it needs to be shorter, three hours is just too long. He's like, But I didn't like how the conversation was gonna be in an hour. I liked having the three hour conversation. So that's what I did, even though it like Yeah.

broke the rule. It wasn't like audience driven. He goes, And so now yeah 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. The host is fake. The interactions are fake. It's just like it's quote unquote professional, but it's the least real thing. And he's like, I don't think people like that, actually. He goes

Podcasts are professionally unprofessional. And he goes, uh 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 think 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 for like kind of forever. And I thought that that is It relates to like

Hassan Minhas 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 wanna be on because I know To do the to win in those games, you just have to dance for the algorithm. Like And he's like I just don't wanna do that. I wanna 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. He's like, you see this in everything. He's like he goes, I w his uh I love basketball. You see this on the basketball court. Guys like Steph Curry or Luka Doncic. They're free. They're just playing how they want to 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's like that's what he's 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 fifty people. He's done shows in front of fifty thousand people, but he knows in front of fifty people. He's having a great time. He's having a great time because he's smoking a cigarette. He's just smoking a cigar. He's talking. He's not even doing planned material. He's like he's having a great time'cause he just likes

doing it this way, and that happens to have gotten him a huge fan base. And he's like, that's kind of my like, if you want to understand what's your strategy, he's like, that's my strategy. And I think that that's just like a more admirable way to approach Like content creation versus this like, I'm gonna just cater to this moving target of like what my audience what what the audience wants. Well, there's a there's there's a way of like not truly caring, but then you also like I like seeing our feedback. We had a guy message us and he's like Someone died in my family and I listened to you guys a ton and th and I'm like, Oh, that's that's sick. And or the someone will be like, Man, I love when you talked about this. I'm like

That's awesome. I feel good about that. I wanna make people feel good as well, while also making myself be selfish and only talking about what I want to talk about. But it it There is a small motivation of feels good to make others feel good. But we're we don't like go crazy on that. Yeah, yeah, yeah. Exactly.

Ultimately who's in charge, right? Like you might have three 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 to sit 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? Alright. To me, that's the highest like order. Decision maker. Sick.

I think this is a good one. What do you what do we want to wrap here? Yeah, let's wrap it up. Alright, we have a bunch of stuff next week. I feel like I can rule the world, I know I can be what I want to

I put my all in it like my day song On the road less travel never looking back

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