Shaan walks through his “decision register” — a Google Doc where he records every major decision, the reasoning at the time, and lessons learned — and shares the full checklist of questions he asks before making a big call. Sam and Shaan then riff on the newsletter business landscape, why most AI newsletters will fail, what made Milk Road work, and how Joe Rogan and Hasan Minhaj think about creating without pandering to algorithms.
Speakers: Shaan Puri (host), Sam Parr (host)
The Decision Register: Why You Need to Document Your Choices [00:00:00]
Shaan: I highly recommend this because judgment and decision making is the most important thing you can have. People are terrible at actually honing that skill. They always say, “Oh yeah, I learned a lesson.” Really? What was it? Did you write down what you were thinking then, and what you’ve learned since? No. We put very little effort into this.
So I have this document — I call it the decision register — where I basically write down every major decision that I make. The very first one I have on the list is from when I was around 20, 21 years old. It says “quit pre-med.” I was a senior in college, pre-med, took the MCATs, but decided not to go to med school.
Sam: The most obviously good decision you’ve ever made.
Shaan: Clearly. We could fix this the obvious way, but let’s try something — stick out your tongue, we’ll use that for your ACL.
So I have a few columns. One says “did it seem big in the moment?” Because one learning was that a lot of the biggest decisions didn’t actually seem big in the moment, but turned out to be important. Then I have a column for “what was the one decisive reason?” — not a long list of pros and cons, just the main reason I made that decision. And then outcome and lesson learned.
I’ll give you another example: the decision to sell to Twitch and not to Facebook. Those were the two final companies that gave us good offers. 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 six years of a startup I was tired, and Facebook was looking at us like we were going to save their gaming initiative. They wanted us to make it happen. But I was like — Twitch has already won. I can just be on cruise control here. Let me go play for the winning team versus trying to take the underdog from the bottom of the league to the top.
One of the lessons learned is: I don’t know what the other side would have been. I know what I got out of it. 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.
Sam: And you’ve been — is this a running document you’ve had for ten years?
Shaan: No, I started it maybe four or five years ago, but I went back and tried to reconstruct things. It’s a Google Doc.
The Investment Mistakes Column [00:04:30]
Shaan: There’s a bunch of investment decisions in there. For example: not buying Ethereum and Bitcoin when the smartest people I knew were literally working in my office and doing it at the time. Didn’t seem like a big decision. I just overlooked it. I didn’t even realize I was making a decision. It seemed weird, so I kind of laughed at it — thought it was strange rather than leaning in and trying to understand: why are you so excited about this? Could I place a small test bet?
Terrible call. I didn’t pay attention to the signal, which was: what are the nerds doing on the weekend? That’s what they were doing back then — they were really into cryptocurrencies.
Sam: Right.
Shaan: So I have this decision register and within it I have a list of questions I ask whenever I’m about to make a big decision. Let me pull that doc up real quick.
Sam: And you highly, highly recommend this because we put very little effort into this kind of thing.
Shaan: Right. I’ve basically realized that one source of alpha is to take a disproportionate amount of time on decision review compared to most people. It doesn’t even take that much time — maybe a couple hours, twice a year. But just doing that exercise can improve my judgment at a rate maybe two or three times what a normal person’s would. And then all of a sudden people are like, “Man, how do you make such good decisions? Where do you get this wisdom?”
Sam: Yeah, you’re so wise. Those abs — you gotta do something.
Shaan: Put it on me. All right, here are the questions I ask.
The Decision Checklist: 12 Questions Before Every Big Call [00:07:00]
Shaan: So here’s what I run through. First: what is the decision? Explain why I’m doing this in tweet length. I have to be able to explain the decision in a tweet.
Then: what alternatives did I consider? Did I consider any alternatives?
Then: what am I feeling? And I have some options — extreme fear, pessimism, neutral, boredom, fatigue, greed, extreme greed, FOMO. Those are the emotional states I might be in right now.
How long have I been thinking about this decision? Is it a few hours, a few days, three weeks, three months, a few years?
Who and what tipped me over the edge? What’s the last conversation, podcast, or thing I read that made me take action?
What are the secondary benefits of this? Like, can I sleep better at night because I’m not worried about a margin call?
If I took away all the secondary benefits, would I still make this decision? Yes or no.
What makes me think I’m right? I have to write why I think I’m right about this.
What might make me wrong?
Upside if I’m right, downside if I’m wrong — I have to define both.
What follow-up decision should I make to make this decision more successful?
How do I predict this is going to play out? I have to actually write out how I think it unfolds.
And then I set a date: when will you revisit this?
Sam: So you can go back and look at it later.
Shaan: Exactly. I did this when I sold all my stocks. I can go look at that right now and ask — was I right? Was I wrong? What can I learn from how I was thinking then, so the next time I can think better?
Sam: How many decisions do you have documented this way?
Shaan: I think I’ve done this maybe four or five times in the last two or three years. Selling a company was one. Making a big financial decision, investing in a private company. Deciding to rent instead of buy a house right now. Things like that.
Sam: Do you consult your wife when you do these things?
Shaan: No. I probably should. She wishes I did. But not necessarily asking for permission — more like getting her perspective.
Sam: Yeah, that’s the problem, right?
Shaan: Yeah. The messed-up psychology for me is that it kind of turns into asking for permission at some point. You have to be aligned to do this, and what if she’s not aligned? Then I’ll just do the thing she hates.
Sam: And how much — when you were selling Milk Road, were you like, “Hey, just so you know this is happening”? Or was it more collaborative?
Shaan: No, I talked to her a bunch. I got her opinion on it several times during the process. She’s very helpful. It’s more the stock or startup investments I don’t consult on, because the context is so hard to explain. She doesn’t pay attention to the stock market, never bought a stock in her life, doesn’t know about angel investing or startup investing. I’m like, the context required here is really hard to transfer. But a decision to sell or buy a company — that’s much easier to explain.
Sam: Right. I consult my wife on this stuff a lot, but it’s more like I just need to speak this out loud and have someone be a sounding board. Like that character on Billions — the mindset coach. Wendy.
Shaan: Yeah.
Sam: My wife’s demeanor is so even-keel. She’s like Wendy. Very third-party about it. I could see her being like, “I’m going to help you with this decision” rather than “This is our decision and I have my opinion.” Totally collaborative, not adversarial.
Shaan: Yes. And I have a history of making emotional decisions, so I need someone to say, “Hey, don’t be crazy. Don’t do this right now. Just sleep on it. Just wait.”
Sam: Dude, the decision register is good. I think you’re very talented at these frameworks. I’m going to probably steal that for Hampton — I think it’s quite good. You should post it in the YouTube description so people can actually read it.
Shaan: I’ll put a link to it in the description and show notes. I’ll make it a template so people can make a copy for themselves.
Small Boy Newsletter Update [00:14:00]
Sam: And that’s at — small boy, is it dot-co or dot-com?
Shaan: Dot-co. And it’s “boy” spelled normally, not like baller-boy.
Sam: Smallboy.co. Yeah, that thing’s growing like crazy. We have like a hundred thousand people on the list now.
Shaan: Amazing, and in a very short period of time. Did you start at zero?
Sam: I started at about 38K from my old email newsletter — Five on Tuesday type thing. And then basically at the start of this year, maybe February, so five or six months ago.
Shaan: Any paid marketing?
Sam: A little bit. I think it’s still about half organic, half paid. But newsletters, man — they’re the best.
Shaan: They’re the best. I take all the credit. One hundred percent of the credit. Not your effort, not your day-to-day hard work. It’s all me just saying newsletters are cool.
Sam: Exactly. I’ll take that.
Shaan: My decision register for why to start Milk Road was basically: I think I know how to do this because I watched Sam do it from scratch with The Hustle. And I thought — if you took The Hustle plus crypto, that would work. That was the whole thing. Pretty sure Hustle plus crypto works.
Sam: Hustle plus anything will work. Just do The Hustle Plus. The Milk Road of business and tech news. Whatever it is.
Shaan: But Hustle plus anything — I think that’ll work for the foreseeable future.
Why Most AI Newsletters Will Fail [00:17:00]
Sam: You know what’s funny, I don’t know how much you get hit up by people doing newsletter businesses, but I’ve learned to ignore them.
Shaan: You ignore them?
Sam: I’ve learned to ignore them because my friend Ramin has this framework: 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. Some businesses are really hard to get initial momentum. Others are really easy to get initial momentum, but then turning that into a valuable, scalable business is really hard.
And because of this podcast, people see Sam did it with a newsletter, Shaan did it with a newsletter — I too will do the AI version of this. Newsletters are very easy zero-to-one businesses. They’re not easy one-to-end businesses.
As I’ve talked to people doing this and they’re asking for advice, I’m like: talk to me in six months. I told one of them straight up, “You’re driving off a cliff and you don’t even realize it yet.”
He said why, and I said: I don’t really feel like coaching this whole thing, but I’ll just tell you — please don’t fall in love with this as it is, because this isn’t going to work. It’s very easy to just watch the subscriber count go up. Or if you’re in a hot space like AI, you’ll get easy sponsorship revenue for the next six to twelve months. But if you want to take this to the finish line — where the thing is spinning off millions of dollars a year in profit and you can sell it for tens of millions — that’s where the real skill comes in.
And I do not feel that most of these people are equipped to do that based on what I hear of their plans.
Shaan: The person who’s done it best, I think, is Austin Rief at Morning Brew. It’s about ten years old now. I think they publicly said revenue is in the seventy to ninety million range. 250 employees. I went to their office — it’s like a beautiful tech office setup. He’s done it all the right way. He’s made a bunch of errors like everyone, but the durability and long-term view combined with short-term speed — that guy’s a machine. He’s one of the more impressive operators I’ve seen.
Sam: The thing is, people see The Hustle or Morning Brew and they just see the tip of the iceberg. Like the iceberg theory: you’re only seeing the top, you don’t see the ninety percent of the mass that’s underwater.
The benefit for me with Milk Road was — I was there when you were doing events and then blogs, and then you pivoted to the newsletter. We were in a mastermind group, checking in every month, talking about what you’re trying to do. So I got to see the five-year underwater build-up. Most people don’t have that. That’s basically luck for me — that I had that access — and that’s why Milk Road was able to work a lot better than it would have otherwise.
Most people are just trying to copy what they see on the surface level. That’ll get you the zero to one. I don’t know if it gets you the one to end.
Shaan: I think if you’re a great entrepreneur, you’ll make it work no matter what. The problem is, you survey ten entrepreneurs and they all think they’re a great entrepreneur. But by definition not everybody’s above average. Maybe one out of ten is actually that person. The problem is, all ten think they’re that one.
The Advertiser Value Problem: Crypto vs. AI Readers [00:24:00]
Sam: What they don’t see is that Morning Brew — to make seventy or eighty million dollars a year in revenue — needs something like eighty salespeople. And if you have eighty salespeople, you also need thirty support people to handle what they’re selling. You also need evergreen content.
The people doing AI newsletters right now are like: here’s the latest demo in AI. Guess what — eighteen months from now that’s not going to be interesting to anybody. And advertisers are going to realize that the kind of person who just wants to see an AI demo is not very valuable to advertise to.
Milk Road worked because people who read about crypto were crypto investors. Crypto investors are a very valuable audience segment. That’s very different from just writing about the new hot thing.
Shaan: Right. Crypto and AI — they’re all just topics. They’re the new thing. But no, they’re not equivalent. The people who read about crypto were putting tens of thousands, hundreds of thousands, or millions of dollars into those portfolios. That’s a very valuable customer. That’s not true with an AI reader.
Sam: They don’t see that. They just see the surface level. They’re not thinking critically enough to realize they’re riding current momentum where every day there’s a mind-blowing demo and people are curious. Eighteen months from now that’s going to fatigue out.
And then your advertisers are going to realize: cool, you’re advertising to a random person who likes to see cool AI stuff. That’s not translating into money because that’s not a very valuable audience demo.
Shaan: And you can’t be mercenary about the content. A lot of people are like, “Oh, I just hired someone overseas and we use AI to make the content.” That’s 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, your thing sucks. Getting people to do that is really, really hard. It’s very challenging.
It’s about getting people to take an action — whether it’s to buy something or show up somewhere. And that’s really hard if you’re a mercenary versus a missionary. If you’re all-in on this thing, that’s why it works.
Sam: That’s why Milk Road worked. One of the coolest things you did was: I invested this much money into crypto, here’s my portfolio, you can see it as we go. You were in it. And you talked about the stuff that each day you were most curious about — that was the only guiding principle. It wasn’t news, it wasn’t announcements. If those were in the newsletter, cool, but the lead story had to be the thing you thought was most interesting. Which was sometimes Twitter drama, sometimes a cool product, sometimes a price analysis, sometimes whatever.
That’s very different from hiring a journalist or an aggregator to summarize headlines.
Shaan: That worked for us. I don’t think it’s the only way, but it felt very different. And like you said — if we said we’re going to be here at this time and date, people would come. Because they were excited to meet us, excited to meet other people like them. The brand had some influence on people, which is what you need to do this.
If you just throw up a quick Beehiiv newsletter and get 12,000 subscribers — the subscriber count is really the wrong metric. That’s the other way of putting it. It’s the easiest metric to look at, but not the right one for a newsletter.
Sam: This is one of those episodes where we talked about stuff I personally care about. I could talk about this newsletter stuff forever. I could talk about personal finances forever. It might be a high ratio of things we love to talk about that maybe our audience doesn’t entirely love — but I’m very eager to see the response to this. This stuff actually interests me.
Shaan: Totally. And by the way, I think that’s the only way this podcast can work.
Joe Rogan on Podcasts Being “Professionally Unprofessional” [00:31:00]
Shaan: I was watching this thing with Joe Rogan. He doesn’t go on very many other podcasts, but one of the ones he goes on is Breaking Points — that news show he likes.
Sam: Breaking Points is awesome. Yeah, I know it. Sagar and — I forget the woman’s name — they’re good.
Shaan: So they interviewed him, and they asked: Joe, everybody does podcasting, everybody does interviews, but not everybody has what you’ve created with JRE. What are you doing differently?
At first he just tries to brush it off — “I don’t know, I don’t know” — kind of fake humility, but also like he’s making a point that it wasn’t some calculated thing. But the guy pushes him. He’s like: there must be something. Whether you planned it or you intuitively do it, you’d agree there’s a difference between what you’re doing and what other people are doing, and there’s a difference in the results. If you had to think about it, what would you say?
And Rogan goes: the thing is, I don’t have a plan or agenda. When I started this podcast, I didn’t think anybody was listening — you couldn’t even tell. So I just had nothing to lose, and I decided to do it the way I wanted to do it. If I’m chilling with my friends and we’re smoking weed, that’s what the episode is, because that’s what I wanted to do. If I’m fascinated by some alien conspiracy and I can talk to this scientist, great, that’s the conversation I want to have.
Everybody told me: it needs to be one hour, three hours is too long. But he was like: I didn’t like how the conversation would be at one hour. I liked the three-hour conversation, so that’s what I did. It broke the rule. It wasn’t audience-driven.
He basically said: that’s what was working, so I just decided not to change it. This podcast is a massive education for me. I have the conversations I want to have, in the way I want to have them.
He goes: that’s how you end up like those late-night talk shows where everything is fake. The host is fake, the interactions are fake. It’s quote-unquote professional but it’s the least real thing. He’s like: I don’t think people actually like that.
Podcasts are “professionally unprofessional.” He just doesn’t read the comments, doesn’t try to do things based on ratings and reviews. He realized the only way for this to be interesting is if he’s actually interested in it. You can’t fake that for very long — it comes through. So the audience will be what it’s going to be.
Sam: There’s also a way of not truly caring but still appreciating the feedback. We had a guy message us — someone died in his family and he said he listened to us a ton during that time. I’m like, oh, that’s awesome. Or someone says, “I loved when you talked about this thing,” and I’m like, that’s great. I feel good about that. I want to make people feel good while also being selfish about what I want to talk about. There is a small motivation in just — it feels good to make others feel good. But we don’t go crazy on it.
Shaan: Exactly. Yeah.
Hasan Minhaj: Be the Comedian, Not the Algorithm [00:38:00]
Shaan: And it relates to Hasan Minhaj. He said this thing to me once. I’m asking him: why aren’t you on TikTok? Why aren’t you more on Instagram? You could be killing it on those platforms, they’re growing. I’m giving him all the logical reasons to be on those platforms.
He goes: I don’t want to be on there because I know that to win in those games you just have to dance for the algorithm. Whatever the algorithm wants, that’s what you have to do. And I just don’t want to do that. I want to be an artist.
He goes: I come from comedy, and the best comedians are free. They just do what they want and they are the judge. They don’t really care — they pick up on signals from how people react, but they are the final decision maker of whether something was good. And he’s like: you see this in everything. He goes: I love basketball. Guys like Steph Curry or Luka — they’re free. They’re just playing how they want to play. They don’t have this constant voice in their head judging it. They’re free to just create.
Shaan: Rogan said the same thing about comedians. He goes: if you watch Dave Chappelle, he’ll do shows in front of fifty people and shows in front of fifty thousand people, and for the fifty-person show he’s having a great time. He’s out there smoking a cigarette, just talking, not even doing planned material. Just having a great time because he just likes doing it this way. And that happens to have gotten him a huge fan base.
Rogan’s like: that’s my strategy. That’s a more admirable way to approach content creation versus chasing the moving target of what the audience wants.
Sam: There’s a version of not caring but also still caring about the right signals. Who’s ultimately in charge? You might have three co-founders in a business, but ultimately, if a decision needs to be made, who makes the final call? On the content side, 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? To me, that’s the highest-order decision maker.
Shaan: Yep. You want to wrap here?
Sam: Yeah, let’s wrap it up. We have a bunch of stuff next week, but that’s the pod.