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 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 you we put very little effort into this i feel like i could rule where i know i could be what i want to put at all in it like a days off on a roll less travel never so i have this list of questions that i sell 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 eighteen years old it says quit pre bed this is sorry my i was twenty twenty one years old so i'm i'm at i'm a senior in college i'm prem med i take the mca but i decide not to go to med school the most obvious obviously good decision you've ever made so i then i have here's the call steve worst doctor you be the worst doctor i'm like we could fix this the obvious way but let's try something to stick out your tongue use that for your ratio alright so and then i have an next call 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 and then i basically have like kind of what was the one decisive reason why if i boiled down like not a long list of pros and cons 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 me another example decision sell to twitch and not to facebook those are the two final companies that had we had given us good offers that we turned out 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 gaming initiative you know they were looking at us to like make that make it happen where i was like twitch is already won like i 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 lead to the top in terms of the this industry and you know then it's like you know one of the lessons learned 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 register now a version of it would be 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 was 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 at like 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 doing 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 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 document up real quick and you've been is this a running document that you've had for ten years 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 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 now like you know you we put very little effort into this and so i i've i've i've root 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 two or three x what a normal person would would would do and then all of a sudden people are like man you know how do you you know like whatever where you get this wisdom from sean you're so good at you're you're so wise you know you're such a good decision making like those abs like you gotta do something yeah put it on me alright so here's the decisions decision that here's the questions i asked for an investment here's what i 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 what alternatives did i consider did i consider any alternatives what am i feeling and i have some options like extreme fear pessimism neutral boredom fatigue greed extreme greed fo right like those those are things i could be feeling right now how long have i've 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 may what makes me think i might be wrong upside if i'm right downside if i'm wrong so 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 basically set a date i says what date will you revisit this and so i'll go revisit this and so i did this for when i sold all on my stocks so i can go look at this right now and be like was i right was i wrong 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 you know like selling was one for example you know making a big financial decision investing in you know a private company you know deciding to rent and instead by 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 the there's like this this is my psychology me is like kinda turns into asking for permission at a point you know like you gotta be aligned to do this and like what if she's not a line 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 her a bunch i got her opinion on it and you know several times during the process and you know she she's very helpful with that it's more of the like stock or start up investments that i don't really my because i'm like man i'll have to explain so much context because it's not an area she pays attention she doesn't pay attention to the stock market she never brought a stock in her life she doesn't know about start 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 can consult my wife a ton on this stuff but i i i think it's more so like i just need to speak this and like i need you to just like be a blank sense a little bit like that character on billions to like the office like wendy like mindset a psychologist whatever i feel like she's like windy like her demeanor is like so even kill yes he's called and like i could see you 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 and then we're gonna figure out what whose opinion is totally yes and i think that i have a history of making emotional decisions and so i a lot of times i need someone to be like hey don't be crazy don't do this right now just like wait sleep on it just wait just wait dude the decision register is good i think you should i think you're very talented i 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 just just make a a template people can make a copy of it for themselves and that's on we'll we'll plug your thing small boy is it dot c or dot com dot c yeah a boy spelled normal or like baller boy not b o no like is it like boy small normal just a small boy dot c yeah dude that thing's growing like crazy mean we have like a hundred thousand people on the list now and it's amazing that's like in a very shorter period short period of time did you start at zero i started forty k thirty eight k i think when you start it so i had thirty eight k from like you old email newsletter five through tuesday type of thing and then basically at the start of this year ish like maybe february or something six months ago yeah probably maybe five six months ago started any paid marketing yeah paid marketing on a little bit of paid marketing i 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 to newsletters man they're the best yeah they're the best that that i take all the credit i take hundred percent of the credit i get what not your effort not your day to day hard work it's all me of just saying newsletters are cool exactly i'll take that i'll take one hundred newsletters 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 and like i think if you took the hustle plus crypto that would work that was like you know the whole thing like pretty sure hustle plus crypto would work secondary benefits hustle plus anything will work like this dude in the hustle plus the or or as you say it's like you're like the milk road of business to tech news yeah you know that 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 feature i think well you know what's funny i don't know how much you get hit up by these people who are doing these newsletter businesses probably all the time i ignore them you're ignore them i have learned to ignore him because my friend has a 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 do you means by that is like 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 cc see sam did it with newsletter sean did it with a newsletter i too will do you know the ai version of this like you know i'll do the whatever version of this users 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'm like talk to me in six months i told one of the air i guys straight up i go you're gonna drive this is driving off a cliff but 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 we'll take like you us a time and like explain what what i think you should do instead i 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 six to twelve months but like if you wanna take this to the finish line where this thing is spinning off millions of dollars of your 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 or 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 yeah 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 it's like a beautiful office like he's has done it all the right way where i mean he's made a bunch of errors just like everyone but that may he's done such a good job of having durability and long term view and also short term like moving quickly that guy's of machine he's one of the more impressive operators so the thing is people see that they see the hustle 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 i was there when you were doing just events and then blogs and then you pivoted to the newsletter we were 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 like build up and i think most people don't have that like that's a duchess 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 one i don't know if that's gonna get you the one to end i i think for most people will not i think if you're great entrepreneur you'll make it working about it 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 get maybe one out of the ten r the problem is all all ten think that they're that 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 year in revenue you need eighty salespeople and if you have eighty salespeople you also need thirty like people 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 and ai guess what eighteen 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 mil 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 because the people who read about crypto were 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 kinda current momentum where every day there's like a mind blowing demo and people are curious easy months now that fit that's gonna fatigue you out that is not gonna be the case that and then and also your advertisers are gonna realize that like cool advertisers of the random guy who likes to see like you know the cool stuff that hey ai i could do that's not translating into a lot of money because that's not a very valuable audience demo 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 that's really hard not possible 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 right 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 right and you're like all in on this shit that's why milk road works because you said i one of the cool 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 what is the thing i'm most curious about that was the only guiding principle it wasn't like news it wasn't announcement like if those were in the letter these other are 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 some whatever and that's very different than if you hire a a a journalist or or an ag 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 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 behind 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 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 this is one of those episodes where we talked about stuff that i personally care about i could talk about those 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 ever and by the way i think that's the only way this podcast can work is like i was watching this thing joe ro joe ro doesn't go one for many other podcast 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 you know like everybody does podcast it everybody does interviews not everybody's having like what's your the like what you what you've created with jerry like what are you doing differently breaking points is awesome yeah i know breaking points yeah saga and i i forgot what her name is the yeah the woman there too they're they're good and so they and what he said 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 you think he's trying to make a point which is it's not some calculated thing and then the the thing i pushes it he's like but there must be something like whether you whether you planned it or you intuitively doing it like you agree there's a difference which 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 what 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 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 or 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 the scientist 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 it's 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 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 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 quote unquote professional but it's the least real thing and he's like i don't think people like that actually he goes podcast 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 reviews are gonna be it goes i realized the only way for this to be interesting was if i'm actually interested in it i that 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 min he he said this thing to me once he goes he goes i'm not he goes i'm like why aren't you want 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 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 wanna 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 comedian they 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 and everything he's goes he goes i he's i love basketball you see it's on the basketball court guys like steph curry or luca 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's like that's what he's like that's like how the best people operate and rogan said the same thing about comedian he goes if you watch dave chappell he'll do these shows in front of like fifty people and he's done shows in front of fifty thousand people but he goes for fifty people he's having a great time he's having a great time because he's another smoking a and chills he's just smoking to say he's talking he's not even doing planned material he's like he's having a great time because 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 wanna to say what's your strategy is 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 audio 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 seeking our feedback we had a guy messaged us and he's like someone died in my family and i listened to you guys a ton and that and i'm like oh that's that's sick or they'll someone be like man i love when you talked about this i'm like that's awesome right 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 feels good to make others feel good but we're we we don't like go crazy on that yeah yeah yeah exactly and just that who ultimately who's in charge right like you might have three cofounder 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 we'll sick i think this is a good one what do you do we wanna wrap here yeah let's wrap it up alright we have a bunch stuff next week if that's the pod i feel like i could rule to where i know i could be what i want to put at all in it like a days off on a goal travel never looking back