00:00
And I highly highly recommend this because, again,
00:03
judgment and decision making is
00:06
the most important thing you can have
00:08
People are terrible
00:10
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, we put very little effort into this.
00:29
So I have this list of questions.
00:31
That I sell,
00:33
I have this document that I have. I think I might have shared this once before, but I call it the decision register
00:38
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 eighteen years old, it says quit pre bed. And this was, sorry, I was twenty, twenty one years old. So I'm I'm at I'm a senior in college. I'm pretty mad. I take the m cast, but I decide not to go to med school. The most obvious,
00:55
obviously good decision you've ever made. So I then I have the here's the call, please.
01:00
He'd be the worst doctor.
01:02
I'm like, we could fix this the obvious way, but let's try something. Take out your tongue. Yeah. We use that for your ACL.
01:10
Alright. So and then I have the next column that says, did did it seem big in the moment? Because one learning was a lot of the biggest decisions didn't actually seem big in the moment. But turned out to be an important decision.
01:23
And then I basically have, like, kinda the what was the one decisive reason why? So if I boiled 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
01:36
learned. And so
01:38
I'll give you another example.
01:42
A decision, sell to Twitch and not to Facebook. Those are the two final companies that we had had given us good offers that we turned down more money from Facebook to take the Twitch offer. Did it seem big? Yeah. It felt big in the moment. Why?
01:53
Because after six years of a startup, I was tired and Facebook was looking at us. Like, we were gonna save their kinda gaming initiative.
02:01
You know, they were looking at to, like, make the make it happen, whereas, like, Twitch has already won.
02:06
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,
02:14
in terms of the this industry.
02:16
And,
02:17
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 registered. Now, a version of it would be, like there's a bunch of investment decisions here, you know, like,
02:36
not buying Ethereum and Bitcoin when
02:39
the smartest people I knew
02:42
literally working in my office were doing it. At the time, didn't seem like a big decision. I just kinda overlooked it. I didn't even realize this was a big decision I was making. Seemed weird. I just kinda laughed at something because it seems strange rather than leaning in and trying to understand why why are you so excited about this? And like,
03:01
Could I place a small tester bet? Right? So terrible decision, bad call.
03:06
You know, and I didn't pay attention to a signal, which is what the nerds do on the weekend will 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.
03:16
Okay. So anyways, I have this, like, decision register Now with it, I have a bunch of, like,
03:21
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? No. I started it,
03:31
like, four or five years ago, but I backed I tried to go back and figure out, like, do I,
03:38
And it's like a Google doc. Just a Google doc. Exactly. And I highly highly recommend this. Because again,
03:43
judgment and decision making is
03:46
the most important thing you can have.
03:49
People are terrible
03:50
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 now? Like, you know, we put very little effort into this. And so I I've I've I've basically realized one edge, one source of alpha
04:07
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
04:15
twice a year. But just doing that exercise, can improve my judgment at a rate, maybe two or three x, what a normal persons would would would do. And then all of a sudden, people are like, man,
04:24
you know, how do you, you know,
04:26
like, whatever. Where do you get this wisdom from? God, Sean. You're so good at you're you're so wise. You know, you're such a good at decision making. Like, those abs. Like, you gotta do Yeah. Put it on me. Alright. So here's the decisions. Here's the questions I asked for an investor. Oh, here's what I have to run through. I say,
04:42
what is the decision?
04:44
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.
04:50
What alternatives did I consider? Did I consider any alternatives?
04:54
What am I feeling? And I have some options? Like extreme fear, pessimism, neutral, boredom, fatigue,
05:00
greed, extreme greed. FOMO.
05:02
Right? Like, those those are the things I could be feeling right now. How long have I been thinking about this decision? Right? Is it a few hours, few days, few weeks, few months, a few years?
05:11
Who and what tipped me over the edge? So what is, like, kind of the last conversation
05:16
or podcast or thing I read that, like,
05:20
made me make take action.
05:23
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
05:31
if I took away all the secondary benefits, would I still make this decision? Yes or no?
05:36
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?
05:43
Upside if I'm right, downside if I'm wrong, so I have to define those two. I say what follow-up decisions should I make to make this decision more successful.
05:53
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 And then I basically set a date and says, what date will you revisit this? And so I'll go revisit this. And so I did this for when I sold all my socks. So I could go look at this right now and be like, Was I right? Was I wrong?
06:09
Do I do 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.
06:23
You know, like selling you, Credit was won, for example.
06:26
You know, making a big financial decision, investing in,
06:30
you know, a private company,
06:33
you know, deciding to rent and set buy a house right now, things like that.
06:37
Do you consult your wife when you do these things as well?
06:40
No. I probably should. She she wishes I did, but I don't.
06:45
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, the there's, like, the the messed up psychology of me is, like, kinda turns into ask you for permission at some point.
07:00
You know, like, you gotta be aligned to do this. And, like, what if she's not aligned? 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,
07:14
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.
07:22
And, you know, several times during the process. And, you know, she she's very helpful with that.
07:27
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 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.
07:50
Right. No. I I can solve my wife a ton on this stuff, but I I I think it's more so of, like, I just need to speak this and,
07:57
like, I need you to just, like, be a brainstorming part. Sarah's a little bit like that, that character on billions, the, like, the office, like,
08:05
wendy? Yeah. Like, mindset coach or psychologist, whatever. I feel like she's like, Wendy.
08:11
Like, her demeanor is, like, so even keel. Yes. She's called. She's like, I could see her being
08:18
very, like, third party about it versus saying, like,
08:22
Like, I could 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
08:30
Yes. And I think that I have a history of making emotional decisions. And so I am 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.
08:43
Dude, the decision register is good. I think you should I think you're 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, the show notes for YouTube and whatever, and you can I'll just make it a template. People can make a copy of it for themselves.
09:08
And that's on well, we'll plug your thing. Small boy. Is it dot co or dot com? Dot co. Yeah.
09:14
A boy spelled normal or like baller boy. Not b o I. No. Like, is it like Small boy? Small, normal? This is just small boy dot co.
09:22
Yeah, dude, that thing's growing like crazy, man. We have, like, a hundred thousand people on the list now. And,
09:27
It's amazing. That's, like, in a very short period short period of time.
09:32
Did you start at zero? I start at, forty k, thirty eight k, I think.
09:36
When did you start it? So I had thirty eight k from, like, you know, old email newsletter, five three Tuesday type of thing.
09:43
And then
09:44
basically at the
09:46
start of this year ish, like, maybe February or something? Six months ago? Yeah. Maybe five, six months ago started. Any paid marketing?
09:54
Yeah, paid marketing on,
09:57
a little bit of paid marketing. You know, still I think half is, like, organic or something like that. So, you know, it's, like, half organic growth, half
10:04
paid growth. There's newsletters,
10:06
man. They're the best. Yeah. They're the best. That that I take all the credit. I take all hundred percent of the credit. I get one not your effort, not your day to day hard work. It's all me of just saying newsletters
10:19
are cool. Exactly.
10:20
I'll take the I'll take one hundred News letters are awesome. Dude, my my decision register for why to start the milk road was like, I think I know how to do this because I watched Sam do this, like, from scratch with the hustle.
10:32
And, like, I think if you took the hustle plus crypto,
10:35
that would work. That was, like, you know, the whole thing. Like, pretty sure hustle plus crypto would work. Secondary benefits. Dude hustle plus anything will work.
10:43
Like, just do the hustle plus or or as you say it. It's like You're like the milk road of business and tech news.
10:51
You know, what's the hustle? It's like the milk road, but for this thing.
10:55
But, no, the milk road, the household plus anything. It's it's all that will work for the foreseeable feature, I think.
11:03
This data is wrong every freaking time.
11:06
Have you heard of HubSpot?
11:08
HubSpot is a CRM platform where everything is fully into Well, I can see the clients hold history, calls, support tickets, emails, and here's a test from three days ago. I totally missed.
11:20
HubSpot, grow better.
11:23
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 him. You ignore him. I have learned to ignore him because
11:32
the, my friend Remind has this great little framework he says, which is that every business is hard. It's just hard in one of two places.
11:39
It's either hard zero to one or it's hard one to n.
11:43
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,
11:54
that's, like, at scale is really hard. And
11:57
I would say
11:59
Because of this podcast,
12:01
people basically see Sam did it with a newsletter, Sean did it with a newsletter.
12:04
I too will do, you know,
12:06
the AI version of this. Like, you know, I'll do the, whatever version of this. Users are very easy zero to one businesses.
12:13
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'm like, talk to me in six months. I told one of the AI guys straight up, I go,
12:25
you're gonna drive this is driving off a cliff. You don't even realize it yet.
12:30
And I was like, he's like, why? And I was like, you know, to explain this to you, we'll take, like, you know, some time and, like, explain what what I think you should do instead.
12:39
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.
12:54
Or, like, if you're in a hot space like AI, you'll get easy sponsorship revenue for, like, you know, the next six to twelve months.
13:03
But, like, if you wanna take this to the finish line where this thing is spinning 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 the people I think would dream of doing.
13:15
That's where the real skill comes in in this. And I think that as 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 MorningBrid.
13:25
It's,
13:27
ten years old now.
13:28
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.
13:37
Two hundred
13:38
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
13:50
that they he's done such a good job of having durability and long term view and also short term, like, moving quickly,
13:57
that guy's a machine. He's one of the more impressive operators. Well, the thing is people see that. They see the hustle,
14:03
and they see just like the tip of the iceberg. Right? Like, 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
14:18
I was there when you were doing just events and then 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 cease the five year under the water,
14:32
like, buildup.
14:35
And I think
14:36
most people don't have that. Like, that's a that's just luck, basically, for me, that I had that.
14:41
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 one. I don't know if that's gonna get you the one to end. I I think for most people not, I think if you're a great entrepreneur, you'll make it work no matter what. 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,
15:03
you know, maybe one out of the ten are the problem is all all ten think that they're one. And, you know, that's gonna be Yeah. They're 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 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
15:21
eighty salespeople.
15:22
And if you have eighty salespeople, you also need thirty, like, people to, like, handle the stuff that they're selling.
15:30
You also need, like, a evergreen content? Like, you guys talk about what's going on in general with general business.
15:37
People who are doing these AI newsletters right now, they're like, here's the latest new demo in AI.
15:43
Guess what? Eighteen months from now, that shit's not gonna be interesting
15:47
at all to anybody. And the advertisers are gonna realize that the type of person who just wants to, like, see an AI demo. He's not very valuable to advertise to.
15:57
Milk road work 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,
16:18
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.
16:32
AC Mus from now, that fit that's gonna fatigue that is not gonna be the case that and then and also your advertisers are gonna realize that, like, cool, advertisers are 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,
16:49
audience demo.
16:50
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,
17:00
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,
17:07
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.
17:16
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. Right. 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 said was I invested this much money into crypto Here's my portfolio. You could see it as we go. I am yeah. I'm in this shit, and I'm gonna talk about that and And I I talked about the stuff that, like, each day, it was basically
17:44
What is the thing I'm most curious about?
17:47
That was the only guiding principle. It wasn't, like, news. It wasn't announcements. Like, if those were in the letter news letter, cool. That's fine.
17:54
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 is sometimes
18:02
a price analysis, which is sometimes whatever.
18:05
And,
18:07
that's very different than if you hire a a a journalist or or an aggregator to basically, like,
18:13
summarize headlines
18:15
from, from stuff. And so, you know, that worked for us. I don't think that's the only way to make it work, but,
18:20
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 date, people would cut people would come because they were excited. 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 beehive newsletter
18:41
and you get, like, you know, twelve thousand subscribers
18:44
and, like, you know,
18:46
The number of subscribers is really the wrong metric. I guess that's the other way of putting it.
18:51
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
19:00
a newsletter.
19:01
This is one of those episodes where
19:04
We talked about stuff that I personally care about. I could talk about those newsletters 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.
19:20
I could talk about this stuff forever. This stuff, actually, it just be, like, totally
19:24
And by the way, I think that's the only way this podcast can work. Is, like, I was watching this thing, Joe rogan.
19:32
Joe rogan doesn't go on very many other podcasts.
19:35
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
19:41
they go, Joe, what, you know, like everybody does podcast stage. Everybody does interviews.
19:47
Not not everybody's having, like, what's your the, like, what you what you've created with JRE? Like, what are you doing differently?
19:53
Breaking points is awesome. Yeah. I know breaking points. Yeah. Soccer, and I forgot what her name is. There's the woman there too. They're they're good. And so they And what did he 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.
20:07
It's just, like, kinda like fake humility, but also, like, he think he's trying to make a point, which is it's some calculated thing.
20:13
And,
20:14
and then the but the guy pushes, he's like, but there must be something. Like, whether you whether you planned it or you intuitively do it. 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 if you had to think about it, if you had to answer, what would you answer? It's kinda kinda pushing him. And he goes he goes, I think that's the thing. I don't
20:35
have a, like,
20:37
I don't come in with this sort of like plan or agenda.
20:40
He goes, look, when I started this podcast,
20:43
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 that were 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,
21:03
Great. That's the conversation I wanna have. Everybody told me, like, this needs to be one hour long. It needs to be shorter. Three hours is just too long. It'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,
21:19
you know, 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 wanna have in the way that I wanna have it. And,
21:35
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 all the same. It's a quote unprofessional,
21:49
but it's the least real thing. And he's like, I don't think people like that, actually. He goes podcasts are professionally
21:55
unprofessional.
21:56
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 or 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 is that you can't fake being interested in it for very long. It comes through. Is like, so the only way to do this is if I'm interested in it, and
22:16
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.
22:25
And I thought that that is
22:26
it relates to, like,
22:29
Hassan Minhash. 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 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, Whatever the algorithm wants, that's what you gotta do. 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.
22:55
They,
22:57
they're free.
22:58
They just do what they want, and they are the judge. They don't care really
23:03
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's like, you see this in everything? He's like, he goes, I will he's I love basketball. You see it's on the basketball court. Guys like Steph Curry or Luca Doncic 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 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, Reagan said the same thing about comedians. He goes, if you watch Dave Chapel, He'll do these shows in front of, like, fifty people. He's done shows in front of fifty thousand people, but he goes in front of fifty people. He's having a great time. Having a great time because he's He's out there smoking a cigarette and chill. He's just smoking a cigarette. He's talking. He's not even doing planned material.
23:52
He's like, he's having a great time because he just likes
23:55
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 wanted to say, what's your strategy? He's like, that's my strategy. And I think just like a more admirable way
24:06
to approach,
24:07
like, content creation versus this, like,
24:12
I'm gonna just cater to this moving target of, like, what my audio what what the audience wants.
24:17
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 that and I'm like, that's that's sick or though 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 wanna talk about, but it it there is a small motivation of it feels good to make others feel good, but we're we don't, like, go crazy on that. Yeah. Yeah. Yeah. Exactly. It's just that who ultimately who's in charge. Right? Like, you might have three co founders in your business,
24:55
but ultimately push who makes the decision push comes to shove. Obviously, you all talk about it. You all have, a a say.
25:02
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. That's
25:17
That is the highest. To me, that's the highest, like, order
25:21
decision maker. What do you do we wanna wrap here? Yeah. Let's wrap it up. Alright. We have a bunch of stuff next week, but that's the part.
00:00 25:45