How the Smartest Founders Are Quietly Winning with AI

now zero to one is very likely in ai you build an incredible tool that no one else can do you can do a million in a week or two i feel like i could rule to where i know i could be what i want to put at all in it like a day's off on a goal travel ever looking back okay so for this episode what i'm thinking this is about is this is sort of and guys is gonna be generous to us but what is the smart money doing with ai and you know in embedding and sports betting in vegas you always kinda wanna watch what are the sharp doing have they tend to be just you know maybe ten or fifteen percent earlier to to to understanding things or to recognizing things and so similarly jason why you on because you've been doing really your stuff with the eye both from investing you're talking to startups that are using him you're reading all the reports but also you yourself built this ai tool and so i wanna kind of get your reaction to a few of the of the different things can you first explain this ai experiment you did where you basically made a body double of yourself out of ai and like what was the experiment and what'd you learn well yeah so so sas has a lot of content as you guys know we have twelve years of content some of it's out of date right for for sure saas being you're a previous founder who's exited multiple software companies now you're like the godfather of like saas because you have this blog and media company and events business called sas and you have a huge fund so that's good the but probably most interestingly for for like seeing the future a little bit is i have about ten thousand pieces of content i've written over the years a lot of it which not out of eight and i update it personally so about ten thousand pieces of content and then we have several thousand interviews like you guys do but with so many great folks early ones with da middle ones from da da went went hubspot just ipo da the other day yam last week but brian hall over the years and we have all of it in our ai took everything i've written every tweet i've ever done every linkedin post every saas video from every speaker for twelve years aaron levy the week he went ipo for the first to last week when we were talking about ai all of it ingested in this ai and so what i instantly saw was as soon as i would talk to this ai it was much better than me it was much better than me because i forget you get that information in there you just hook up rs right the feed for blog it can scrape the web which is pretty easy soon we'll be able to do other things like mc but it's just scraping apis and rs really just scraping you just give a url but did you use like delphi or you you built your own tool or what what'd you do i tried a couple things and then i used delphi and then at first we had so much content it was a little difficult to ingest it so there is there is a little bit of work and then i spend about ten minutes a day training it which we could talk about so there is a little bit of maintenance involved but it's better than me and the thing i didn't get until i saw something that was hyper trained like this is a lot of content twenty million words right very few mistakes very few hallucinations and the ability to connect things that i can't i just don't remember i don't remember what sam and i said on the hustle on stage years ago versus when we did an m while versus today but the ai knows at all by the way twenty million words is like two hundred books worth of content average i think it's like a hundred thousand words so twenty million words you're saying is you basically gave it twenty two hundred books of your own brain and the brains of other guests that have come on your show yes and your goal was to build was it to build basically an adviser an ai version of you that could be an adviser to a founder who wants to come and talk to your ask questions but you don't have enough time of the day to book calls was that the big of i just wanted to learn like you guys i just wanted to learn i didn't think it would be as good as it was because i used other products and i've used other things and it wasn't as good as my my digital ai was it was wasn't the use case would be what is it what i said or is this something else the other interesting thing is the use cases with ar are much broader than you'd expect okay so i didn't expect people to upload their board decks before board meetings and asked for feedback before board meetings that's an niche use case i didn't expect hundreds and hundreds of founders to use it as their therapist for their company where the growth has slowed i didn't expect that i didn't expect so many folks to use it to review their sales scripts their sd scripts when there's when there's specific tools to do it right i didn't expect it's so good at reviewing vc pitch decks it's so good at it better than anything i've seen can you get tactical for one second so you got at delphi dot ai i u and you just uploaded the saas rs assess feed and it did all of the work you youtube rs twitter blog blog but but could i go to a health guru or a business guru who i subscribed to who i love then i say youtube dot com slash alex from upload that and it automatically does it is this well it's interesting question it is prohibited right it is prohibited by their website their terms of use they prohibited it but honestly this is an ai risk we you could you could do it absolutely you could it you could redo what i did it might take you a little while longer but you could just clone exactly myself yourself and then you would you could do it just as well as i did sam i've never felt so used and abused when jess came on the podcast that she was like yeah actually i have my team training in ai of view so that if i'm brainstorming ideas i don't have to ever call you i'll just ask the ai what you know basically you'll just be in the meeting with us yeah it's she's like we yeah we just took all the podcasts and we're training it on how you think the questions you would ask what you would say reactions you would give and now you're just there in the meeting so she basically hired me without ever paying me right because i have this corpus of content out there i put my brain out there in the how do i do that like how do it can't can i just upload a youtube channel and say this youtube creator has great advice and i could upload eight hundred videos and it will transcribe all of them i could go it may take a a day or two to fully ingest all that content but it will do it just from the url of your youtube just on delphi dot ai i so i can i could make i think it is a great product there are other people that can do it too that is not there are i'll tell you what i think is interesting about delphi but looking at all this cursor and win stuff and lovable and like you don't realize like they're just so far ahead of like b to b and regular people only because they're better people working on them if we have the quality of people working at winds working on on crm okay or working on marketing tools or podcasting tools your jaw would drop today but this is why your jaw is gonna drop over the next twenty four months because just mediocre engineers cannot like the open the the engineers at open ai are so good they're just so good and so but the average engineer working at a struggling crm right is just not just not that that good but they'll catch up but yeah you can build all of this and here's the interesting learning so we could build a digital sam and and we could do this for next week or whatever you can do it the my learning from my eye it's okay that it's not you this is why for example you can train your voice it uses a level eleven is that the product or love i get a little confused the eleven right yeah eleven lab eleven labs yeah eleven labs and level labs is epic right but you can choose you want it to be exactly like you which is what brian hall did and then i realized that was creepy i don't want digital jason to be me i want digital jason to be a prime version to me that ninety percent of the time is much better than but is distinct i don't want people confused like brian i get can like brian hall and so it's okay that it's not sam like it could be a version of sam that is better than sam so okay let's walk let's walk through these top ten learning so you build this ai it has thirty five thousand conversations with people you did like fifty now we're have fifty thousand conversations and learning number one you said users will tell ai things that they won't tell humans what i mean yeah well first of all before we can get there one obvious like there's no way i could do fifty thousand conversations is there alright i'm not even a people person i could do like one or two a day and i get tired fifty thou just think about the delta between two a day and fifty thousand but yeah this is the thing like there are some things that are somewhat unique about me that are early the amount of content sound like your math right the amount of books we're talking about here right the amount of content i've written just about b to b just about biz building business software the other thing is there's enough people i'm not like a super influencer like you guys are but there's enough people that know the digital me that they already know what to ask me right they've already watched me in event they've read the content so like they ask me things without thinking it's a prompt or prompt they just ask things they want to talk about their deepest fears like i i've partnered with sam on this podcast but i'm not sure committed is me i see him doing other things he's into this accounting software and this hampton thing i'm already quit my podcast on me what do i do and my ai is really good with talking that through you right so people just how does that all this sam hey hey jason the heart there jason you think it's funny but like you might ask jason jason how about you shut up well now you put there there are thousands of these types of conversations my founder is not as commit my i don't know if my board's gonna fire me right i is is i'm only growing eighteen percent i eleven months one way right are you zuckerberg burger here how do you know what they were saying it was just some privacy here how do you know what's what's being said it is interesting and on this app you can set how much privacy you want you can minimize everything there you can no because there's different use cases if you're using it as a support tool think about it using as a support tool you don't want an anonymity for how can you follow up with someone right right then there's like a therapy level where you would want true anonymity and then there's like a everything's a slider an ai in in a sense right i think that i'm like you said the therapy thing as if it's like can you believe that and yeah i'm like dude i use open a c fatigue for therapy three hours a day yeah like everyone does like the majority of i'm like this email pissed me off how do i reply in a graceful whole way or like i argued with my wife or i'm upset about that i'm not doing this like like the other day on sunday i saw someone who had a super fancy home and i was like how do i get over envy do you know what mean like like that's all i use it for it is and this is the same thing it's just because it's got the twenty million words for business to business content sales content scaling your revenue it's it turns out this and this was a surprise to me i didn't believe this it's better much better than chat gp it's much better and you you you said something like you trained it afterwards can you just what do what do you mean by that how did you train it afterwards well listen i'm gonna embarrass myself technically okay but basically those twenty thousand words it you basically rag it okay you twenty million twenty million or twenty twenty million words of my content you turn it into a a a a a very a database instead of and and you just add that to chat or claude or deep sync and the way you add it and the relative weights of my content versus the generic content radically changes the output but like chat gb never asked my permission it's already slur up all my content hasn't it every single youtube is in chat g everything i've written i have been paid a nickel so what's interesting is that content already there but by i weight by heavily weighting it toward my content for my type of knowledge it's much it's not a little bit better than chad tb it's like much better right how do i just how do i create a sales comp plan i have four sdr str r's and five aes our our our average deal size is two k a year and we wanna go from two million to six million next year and and my team won't really do outbound chat is gonna give you a very mediocre answer but my ai is gonna give you insanely good answers even though overall we're pulling from the same content right and so you you had to do that manually was that the training or did you do more did you do more training than just that well first of all it auto updates every day which is better than chat eb or claude it auto updates every day it slur up everything on my blog on my social media on my youtube every single day it does it essentially almost in real time okay and then yeah you it does it itself it auto updates now what i do here's what i do is and it i'll tell you my learnings on my hallucinations okay i audit a few of them i read some and i see if they're wrong right i see if the ones that are that are not anonymous if they're wrong and when i see something that's wrong and i'll tell you what i learned if you're interested then i there's a section where i just train it right and i say no sam and i first met in two thousand and four sixteen after i wrote a quo post and he had me do a meet at the hustle okay because it got it wrong and made something up okay so i do i do have for about ten or fifteen minutes a day and it turns out it doesn't get very many things wrong and the things it does it consistently gets wrong and i'll tell you why and then i just fix it and the next day it's right then if you do nothing and you don't train it and you put no content in yeah this biz this this average vp sales is gonna say yeah it doesn't work you know i i i log in to chat a year ago and it and like you're gonna lose your job but the hard the hard part here is like so i'm so committed to chat gp so it it it it knows so much of my information because we've had so many conversations it does are we all gonna have like files you know like our health record where it's like you know my the background because it sounds like i get nervous to switch to any other model because i'm like chat i've already asked so many questions it already knows everything it's an interesting question here's what i've learned first all memory is a big deal right chat could already remember questions but now it's remembering everything okay it's so so it's a emo from the top folks i've worked with on this there's on the one hand it's a it's a moat just like beam in the google ecosystem is a mode just like back being back in the day beam in the yahoo ecosystem was a emo okay but the mode is not as deep as we think our ability to get to get trained and up to speed does not require twenty million words so yes it is a moat but if you decided claude was much better for you and you the point is and you spent a month just including your day each day you you're probably there you're not not a hundred percent it's enough it does somebody have startup idea i think it was erin levy or something somebody was tweeting this they they were talking about plaid for ai tools so basically you'd be able to just like the way plaid lets you connect your bank safely to any financial service to be able to take your kind of memory and context what what chat knows about you but port that to some new app that you're trying without without handing over everything but allow it to pull from that and i i was like oh that's a that's actually a very interesting idea if apps will even exist in the future well what will exist instead of apps why we're going through a transition phase right we're going through now we're chatting once again we've been chatting since the ic days okay since ao we've been chatting in our keyboards with people now with ai we're chatting again okay but we're starting to not even know where we're chatting with right right now already like mc is new but already today open and claude can pull from other apps like hubspot and others and and notion and just pull the data out i don't have to go to notion or even google calendar or hub butt anymore right right as we live in this and then you know people think this johnny i think for six billions crazy it's a great bet because we're gonna go from twenty minutes a day twenty two minutes a day in chat to twenty four hours a day in chat eb and when we're in chat twenty four hours a we're not gonna like pull up a crm we're not gonna use the interfaces like these interfaces are all already dying you can see it sam and the amount of time you spend gp like then go to like a b to b app you're pulling your hair out it's so dated isn't it yeah it's so dated already it's only twenty twenty five and it's already dated to go to any b2b b app they're all gonna die how does the excitement in rate of change right now compared to i don't remember if you were involved in ninety nine in the year two thousand but you're you were close right yeah i was a kid it was my first job back then yeah so how how's is the because everyone talks about the dot com boom and i never got to i mean never experienced it but how's is this how's is this today compared to then those days were the were the first time until i where people feel like they could just do something out of nothing like it was miraculous it was miraculous and that is what ai is like today people are just doing miraculous things and it's exciting but man it's super scary for incumbents it's super scary for incumbents do you think that everybody who is maybe a content creator at least yeah is gonna have this sort of like stunt double this this intellectual stunt double the way that you created here do you see once you've did this experiment are you like this is the future or this was novel but no i don't think it's gonna last like you know where where's your where did you land after the experiment i well first of all what i think i'm not a consumer content creator i don't think anyone is gonna create content without ai going forward and the tools are gonna change like for example just for for our last big saas event like i did all this speaker promos and hicks they use higgs field no it's incredible how do you spell that higgs field dot a it's the x head of ai from snap it's one of the coolest apps on planet earth everyone's talking about this new google video thing right but they were already doing it higgs field dot a all you have to do to higgs field dot ai field is i can take a screenshot of us right now i'll put it in higgs field and it will create a movie out of it okay and it will and you can and there's a lot of different ways but there's a really simple way you can do you can take a an initial photo and an end photo and it will just connect them with an narrative so i had like i would take like a picture of yam just off her head shot off hubspot and then take a picture of like a stage at disaster and it would just make a video of of yam wave into the crowd and running on stage on saturn and being excited and so a year ago all the all the digital promos were static you know classic static heads shot with some chrome around it today everyone got a video a really cool video right next year it will be me and yam talking for ten minutes about ai and neither of us will have had the conversation it doesn't mean i won't exist but of course that's already cup we could already almost do that but i did all these things now i did instead of waiting for our designer two months to do a static thing and uploaded it to dropbox and me forget where it was and lose the url and have to do it now i just did it myself in higgs my ten seconds so looking at higgs field this is this is insane it's beyond it's so good so good this is the this is why ai is exciting because the really bad ass people can do crazy stuff now it used to take a badass person like six months to do a prototype and then two years to get it good now someone epic like the x head of ai and snap like what you can do at higgs field will blow your mind right dude i can even tell just why the way you're talking i feel like if we did the same podcast you know five years ago yeah your rate of talking would have been like ten beats per minute lower well did two years ago there's a baseline level of excitement that has just risen like our new blood pressure is here well as long as i've know jason you were borderline grumpy like you were pissed you were pissed off all the time like i i yeah yeah yeah yeah you were like look like i remember you you weren't tired but you were you were tired of people asking you dumb shit because you always had this you had this energy of you where you were like talking to someone and you're like you're making mistake stop this you're making a mistake you had like this like almost angry and you now it's the exact opposite now you're you're optimistic i am i am you you're right i i i'd like to think of differently but you're probably right you the way you perceive me is is important it it is i am very optimistic about it but the difference is i used to think all these products were durable that they were durable now i don't think any of them are durable so what's does that mean when i first started doing this saas content i've made up this expression which i stole from the mayor of tel aviv and people have used it ever since zero to one million in revenue impossible we don't need another product okay one to ten million dollars of revenue unlikely like there's so much competition ten to a hundred million inevitable from impossible inevitable we had a book that's sold a couple hundred thousand copies that was this theme so you go the stage because what i learned is a b b fad you're saying get getting from zero to a million is really really hard yeah getting from one to ten feels impossible but one ten likely yeah unlikely but once you get to ten it's inevitable to get to a hundred if you had good founders it was a punch guard now it's disrupted now zero to one is very likely in ai like it's like you build an incredible tool that no one else can do you can do a million in a week or two but like now everyone beyond a hundred million is getting disrupted there's so many software companies at a hundred to two hundred to three hundred million in revenue that aren't growing anymore it never used to happen four or five years ago like you hit your punch card you had hundred and twenty percent revenue retention and you had a brand all you need was a brand and revenue retention and products changing about every five years right if the product changed every five years and you had a brand and tens of millions of revenue that mean you had you had product market fit right high revenue like high environment meant it kept going as an engine and this this one hundred and twenty a hundred and thirty percent revenue retention it just kept going it took you from twenty to thirty to fifty to a hundred and it was like and that's why you know in in you know this crazy twenty twenty twenty twenty one the average public saas company traded at seventy x arr public in twenty twenty one it's it's almost unimaginable today when it's at five right right but it's because it worked then like everything just worked and now you know i i you know o growing ten percent salesforce growing seven percent like the the they're good companies but it's not durable the way it once was so are those companies my premise or what i thought and what morgan stanley i i thought because morgan stanley had this report which who the gives a shit about morgan stanley but they said that the majority of value creation in terms of market cap for ai is going to be the big companies using ai to get better versus new ai companies do you disagree with that i think that right now today as we record this there's a hint of truth to it and and but salesforce is not accelerating okay o is not accelerating lots of folks are not accelerating servicenow has a lot of ai but it already had workflows that were automation so people say that and there's there's there's there's there's qualitative proof of it but we haven't seen it in the numbers okay so there's a window for the big guys to leverage this because the the interface that we talked about is dying people are not gonna wanna use these dated interface is anymore so even if it is benefiting the big guys today what is the value of of a crm if i don't you log in to the app anymore if i just talk to to chat and i say give me the ten deals i have to work on this week like how valuable is one serum over another or well i even know i have a crm like it just becomes plumbing in a database here's one problem let's step out and i'll one problem with ai one problem with ai is there's been too much nerdy nomenclature the last year too many o o fours minis o three max l dude it's so complicated it's like yeah it's like knowing the difference between an iphone thirteen and on iphone fourteen it's all that's all going away this year it's all that complexity made sense as crazy as these numbers are ant t went from one to three billion in revenue in five months they just announced one to three billion in revenue in five months okay and that is basically all infrastructure plumbing revenue so when the in when the in the area of infrastructure you need to know the difference between the models and r one in this we're just starting the application age and in the application stage age we don't we won't care what models hubspot uses we don't even hubspot already has a lot of ai do know what models it use you don't care right you don't care so the so so these nerdy terms are gonna fall away but what think of mc as the next generation api and what mc does is it lets any ai or others talk to applications without having to right inside of the ai so right now if you go to now that's it's just rolling out but if you go to and you set it up properly and it's still a little nerdy okay but right now from chat you can change your google calendar you can work with notion tell you connect it with m you just well i could i can't quite do it with you on online maybe in two months it's literally when you owe off in it will do it automatically but i can show you off offline you just connect it to your google calendar and then there the the it's still a little bit of a headache around authentication and security like the there's a little bit of magic to go but not much and then you can just talk to your calendar and check and hubspot has announced this so da but what are you using to connect the two so mc is a protocol right so it's like a language imagine this right like you know we have english we have spanish then when the internet browser came out i was like hey there's a new language we're gonna call html yes and you gotta learn that language if you wanna tell the browser what to do how to show a web page right so now mc p is a new language that came out that was basically saying hey if you're one ai app and you wanna talk to another application how are they supposed to talk to each other mc became a protocol that now any app who wants to be like y if like hubspot for example they want all the ai tools to be using to be integrating in with hubspot they don't wanna one by one go work out a deal and do a technical integration with each one so they say oh cool we'll we'll also speak mc we we we understand that language we know how to do that cut writes basically like how apis work for for most websites but mc is like the ai specific version of that right now to integrate with and i haven't ever used hubspot api but i i'm sure it's a great one but but that is bespoke like each one is different hubspot apis different than salesforce and notion and linear you have to learn it you have to get a key you have to code to it you have to understand its nuances it's a lot of work right like you you may know startups ups you general you're like why don't you have a hubspot integration well because it's work right right with mc p it's early but it's just starting it won't be any work you just tell mc to go talk to hubspot or go talk to notion and it will just do it and all that work goes away so if your ai can talk to any app you use take all the data out and let you talk as a human for ninety nine percent of the world we won't use hubspot like the way we use it today there's no reason to log in to this app figure it out like how does the ui work what are these tabs how do i configure a tab and and the kids these days will never know this like this generation coming up they will never use software like we use it they will never use it what are what's the office of open ai like right now because you're saying like well it sucks right now but in sixty days it's gonna be the best which is insane so how many people work at open right now and actually sean for you as well have you guys been to the office what's it like they're at what's it like at that office right now if they're able to do all these things so fast i think it looks like they about forty five hundred employees i'll tell you what's super interesting they only have about sixty percent employee retention over two years because what everyone's going and doing their wrong thing probably but it's just create like an open as sixty percent team retention what's your hope to keep your yuri it team you better treat him really well so i have a friend who told me about the early days of twitter and he basically he had built a company he was like scraping twitter and he was like oh this is cool if based on what people are saying i could figure out what's it's actually trending in the world and the way he did it was he was like you know if people people always talk about new york so if it's if i hear new york a thousand times that doesn't actually mean new york's trending it just be york's already big but if suddenly everybody's talking about tallahassee well tallahassee doesn't normally get talked about that much but it's being talked about as much as new york that means it's trending and so he had a separate site that was trying to figure out what are the trends on twitter now this they ended up getting bought by twitter and that's now what if you go and twitter twitter has trending right so my friend ab was just i was like what was it like in those days and he was like i thought i knew what a startup was i thought and and this i related do this so much he's like basically i thought a start was i wake up every day and i gotta go try to get some growth and i'm pushing i'm pushing i'm pushing the product forward pushing the marketing forward i'm pushing my product out into the market push push push he goes then imagine like you know you think you're pushing and then suddenly you're pushing a bolder up amount and you look up and there's a giant avalanche coming at you it's pulling towards right it's coming straight at you and so he goes my first six months at twitter he goes i woke up and i had the curly keyboard like imprinted on my forehead like i just fall asleep at my desk and i'd wake up and i'm back at work right he's like basically that's how i lived for like six straight months because and he's like everybody's basically front of us because the twitter had the fail he's like but you there's nobody had ever scaled the service like this this fast and so we just couldn't keep it up and we was like we were trust me we were trying everyone thought we were being lazy or stupid he's like we are the smartest people we were trying our absolute hardest and it was just so so difficult and i think what's happening with a lot of these ai companies is that you know sam you and i i think we probably only really experience push for the for most of our startup career yeah it never felt like i was holding on it felt like i was pushing it again a little easier subtitles but it was always resisting like i have this company now we haven't announced this and i just like we have this ai bought that will come and tell us our new contracts and our new revenue last week we closed a million dollars in new contracts in a week and i was like i have never felt this level of pull ever in any business i've ever done and we're not working ten times harder it's just that like the market wants this type of product at a different level i'm am sure that the folks like you know open ai and all these ai star start going they're experiencing a startup up experience side is not we it was not anything like what what you and i experienced sam i think it was zero to eight hundred million users in seven months is that what mary meek said yeah i think so i just wrote it up on twitter we could look or x but yeah ten percent of the world ten percent of the world in eight months or something like that that so that's why the rate of change is so high that everyone that's like a lu night or a debbie downer is missing the point right and before it looks it was a bunch of l loose like people were going and testing the product but it wasn't really high retention and then they've showed that like the the actual it's not just the users that have doubled but the usage per user has also doubled right so you have like a a a double of a double and that's it's pretty obvious to me now that i've kind of an idiot for not investing in this company even at really any price point like this is this is basically the facebook of this generation right like yeah i don't think we realized that open that chat gb would have eighty five percent market share at the pros consumer consumer level that that way that's what that what all that meant to surprise if we if we know because ironically chat g was an experiment it was a proof of concept it wasn't really meant to be the product the the the the center of open ai but like do you beat yourself about this too like the way do because i'm i just look back i'm like how much how many hours have i spent thinking about ai i'm supposed to be an investor you know like you're a saas investor this is the greatest saas you fast saas growing business ever are you an investor did and did any of you have the opportunity to invest in you can hunt it down you know that's on best you could yeah for me i wanna life is short i wanna own ten percent or more of a startup up and have fun so hunting something down just is not my vibe but but it's the way to make the most money don't get me wrong touch wrong with hunting it down and and someone was never heard of shot or my first million and just getting some money and like that's smart way to do it but bet you i bet you da so i think on the pod da mesh i don't know if he explicitly said fifteen million but he sort of wink at it when we when we said so he owned chad dot com which he's sold to open a for the what he paid for it which i think was around fifteen million and he got ai c stock yeah there's a world where that becomes worth like in the ballpark of his hubspot stock i think you know that that does it probably right i it's none of my business but i remember thinking with aaron levi was one of my favorites you know he was early in stripe early in gust like just back in the day aaron had a window before box went public where everyone went to him and he had a little time like he wasn't it and he just did all of them and i'm like man if this guy did stripe in the seed and get all like how that's gotta be none of my business gotta be worth even more than his box doc doesn't issue be four percent of box i think when it went public he's been grinding big box for like twenty years i love him for it yeah wait so he he on the stripe investment there was a window listen it's none to my business but there was a window i've been doing this long enough right we're before box ipo he had time right and then you just skip you just can't do this stuff on your public right baby mark ben can and so everyone he was the guru right he was the one guy he was and everyone wanted aaron and so he would write these checks and you know but i know i we could look up but i know he did stripe and gust and the seed round and a bunch of others and it's sent up my business but i'm like that's there these moments in time that could be worth more than all of his his box shares and so it just gives me even more respect to keep going because so many founders these have a different relationship to money and investment than a few years back and a lot of founders would quit today if their investments are worth more than their founder stock a lot of them do quit a lot of them do quit now you know this reminds me of so it took me at the hustle i think it took me three years to get to a million subscribe a million users and that was like life changing for me to get as fast as some of these guys are growing it's like literally like that per hour and it's sort of like when you see a billionaire who's worth like four billion like four point two billion billion and you're like and that point two divided by ten would be awesome for me do you know what i mean like it's so it's like hard to grasp how big and how fast how how how big these things are and how big they're and how fast they're getting that big well look it's slightly under discussed and it's a cra topic you might have discussed it sam otherwise but like it's a cra top like it's right apartment because open ai will be worth your filthy pick oh but when when when hubspot i i've been around long enough to everyone in hubspot ipo and it ipo about it in eight hundred million dollar valuation okay today it's worth like forty billion but now like open eye be worth a trillion so my point is that the rich are so much richer right they're the like the regular person's like a little bit richer intact and it's great right but because the big wins are a hundred or a thousand times bigger than just ten years ago just ten years ago the amount of billionaires i wrote up on saas the amount of billionaires just in saas cloud i could find this post but your jaw will drop how many billionaires are in it just because the mark the the numbers and markets are so much bigger right there's already a hundred billionaires in b b software i wrote up a hundred billionaires for the people listening what what personality types are like who who's poised like what twenty what does the twenty two year old today looks like who can pounce on this like what's the what's the profile type or the personality type of of these people that are just excel like crazy i think it's just two things and the it really probably hasn't changed since bill gates days or starting microsoft but one is you have to be able to ship insanely good software which maybe and some business software wasn't true for a while insanely good like higgs feel that you're trying chat edd this is not trivial stuff okay this is like insanely good software and then the second one is you have to like be relentless to owning a market there was a while in twenty twenty twenty one we're like being third or fourth was great alright like things were so good that like you you'd be like wealth if i'm never four the market but don't have to sell out of stock and it's comma and i could sell my company for four hundred million that's better than ipo like the now the the best founders day are relentless to being absolutely number one in destroying and owning the market right and because the markets are bigger it compounds to something crazy right i mean again just one example it but sandy and i are both investors and owner and like you know adam was what whatever you know high school dropout starting this company i mean he's gonna disrupt the entire restaurant industry he's already on the way there not being number four and he has an incredible technical cofounder now an incredible engineering team and that product to owner here's interesting because i invested in the seed round in twenty twenty one adam hates it when i say this but the product was not very good dean was very good the cto it did a lot the product but it was not very good the reason it killed all its direct competitors not indirect it hasn't killed the big ones is just because the software is so much better and that just compounds every quarter and ai is accelerating that even faster so you have to build epic software but if you destroy these markets that's that's the path but i just don't think this is a good time to be number four i i could be wrong i could be wrong but it had its age it had its time i i actually disagree with you i i i know i think i understand your sentiment which i agree with but i disagree with how you're phrasing it of there is it's not great to be fourth or fifth place whatever we've had a bunch of people on this podcast that have built apps that were really fast money grabs where they got really big really quickly with tiny teams and what i would tell them which who what the hell do i know but i would tell them i'm like this doesn't seem durable but so keep your team small and ride the wave and take all the money and like do do something else eventually but it's a little bit different than it used to be because you don't need to build these huge infrastructures you can have one hit wonders that crush it you know what safe you have yeah i think what wonders the wrong phrasing but i know what you mean which is that you can yeah a base hit now can provide you enough cash flow to a change your life and b set you up with like five more doors whether it's investing or it's reinvest into another company you start and it you don't have to build one twenty twenty year durable company in order to to be a winner anymore so i think i think i just i to say like back when we were in san francisco early on like the small lifestyle business would get you the equivalent of a job now it get you the equivalent they like you would make a couple hundred thousand dollars if you were had a lifestyle business you know that was like it was working but it was small and it was solo as bootstrap now those same solo bootstrap i like eight million arr so it's just a different scale that i okay i remember what you know the difference is though that that is i think that term is you have to be thoughtful about it in the age of ai when there's so much competition you can build a two or three person company that's small but the lifestyle businesses are being slaughtered because when these three kids come to s f working in the mission and they're working eight days a week and they've taken your little idea but made it much better your lifestyle is gonna be unemployment so this term i think needs to die it it made some sense i think a few years back it's okay i just worry people are gonna take the wrong lessons from it you have to work start this conversation you can do more with fewer people but you better work harder if there's comp you or find a space with no competition right but the weird thing about ai is is there's competition in spaces that two years ago had very little competition like what's an example that comes to mind i'll give you an example i in when i started investing i did a couple investments in legal i knew a little bit about legal okay and no one wanted to invest in legal they're like oh it's takes forever lawyers don't buy anything that takes forever it's boring it's a slow market now there's a five hundred ai legal startups and there's reasons for that but you could not be at that sleepy pace same thing i've done some of the best investment i've done has been in support in post sales okay no one wanted to do this type of start boring resolve tickets pick up the phone right now there's thousands of voice startups there's thousands of these and so if you think you can run a lifestyle customer support startup good luck right good good luck because delphi out of the box is probably better than you you you own a a media company you you own basically if a trade show that's incredibly successful so let's just categorize that as a boring company that is not a technology company for sure which is which is what i do as well and sean has done something like that in the past as well i believe for the people like like that how are you using ai in like a bolt in a in a in a not tech company are your employees now becoming significantly more efficient i mean we only have two people now i take it back we have five people and we do five million per person now did you have more people before you much more people before we had people in twenty twenty runner out even we have four designers now we have a little bit of a designer in ai tools we used to have five people on this content team reviewing sessions now we have zero now we just have ai so we got we have none of the designers none of the content people all the ghost writers are gone they're the worst right well i write my own content right let me drop you off a bear airport but what happen let me go reverse order like okay nine months ago yam would come to a saas event she's done it three times okay and she would speak and three months later a ghost writer would write up a terrible summary of her thing just terrible and i would cry and we'd ask them to fix it because i can't do everything right and then about nine months ago they got better they actually they got they weren't great but they got better and i hadn't actually used claude and then i went into claude i'm like this she just put it in claude and they store charging us five thousand dollars a month for this so like we can do this for twenty bucks in an hour instead of five thousand dollars and waiting two weeks with our clients right so we didn't need the ghost riders we got rid of first right then we had five people then we had an agency we worked with for years and for while was great and they would review all these speakers a lot of work to work with speakers you've done sam and when you have hundreds and hundreds of speakers it's impossible to do it all right but they decided they just didn't wanna work that hard anymore so they they wanted to charge us two to three times more and only do half the work so it just didn't help us right so then we're like we're we're o now we're five months before saas annual and we just said well let's have our ai do it and it it reviewed three hundred sessions three hundred slide decks three hundred presentation you have to chase those three hundred people down to you the yeah we still have to like it doesn't get rid of everything but it does ninety percent of the work and it better and it does ninety percent of the work three times better ninety percent of the work three times better was that you the business owner who had to architect and come up with dolby these solutions between emilia who runs faster this media business and events and me yeah we came up no one else was like motivated to do it of course and that makes sense and and then like we have a you know we have a little bit of a sales team but then ra just started to do all the screening and initial sales conversations for us that helped a lot even for it's this is a very niche business trade show business exactly so you do twenty five billion in revenue with five employees is pretty breathtaking because i would have thought that would be on the lower end your business would be on the lower end of like well i still need people but you have just proven that not to be true and so it could do better with more people it could do better with more people it's out of your life your life gets worse no honest honest i don't need to get off target the real problem is i just can't it and sam this is why you think i'm g because of early conversation we had i've just struggled to find enough a tier talent that wants to do this non sexy stuff okay would love to have twenty people on the team tomorrow i a budget for it at least fifteen but but i don't need someone that shows up to a meeting with the sponsor and doesn't know what we do okay i don't need a designer that doesn't finish the the design until after the event which i had once in past like send us a big bill but didn't finish the assets until after the event i just don't need that right you know i just don't i don't need i don't need someone managing ten thousand people in in our in our disaster annual that forgets to do catering like i just don't i'd rather have the ai come up with the cater the ai did our catering schedule this year well could you talk about the start of disaster real quick so when you started this thing you had sold your company yeah right or was it i was it after you sold echo sign or a long time ago twenty twelve but yes so twenty twelve you sell your company a great exit i as i understand you're like i've i've retired twice i got in shape i picked up a hobby and realized you know like i still love building so so you sell your company do you retire right away basically you could take a break well after there's probably a little bit of parallel to sam here both times after i sold my startups i sort of didn't work for the better part of a year and just got restless for different reasons right and i just got restless and in fact both times after about a hundred days hundred twenty days i got a little depressed maybe depressed is too strong word at lost lost right definitely lost i remember you know my second startup up emergent capital which is a very successful b to b venture firm had a ceo every year had a big ceo meetup up right where they would come and and my in my class my group by a david sacks and aaron levy and peter gas from vi renee and then after i got acquired i got to go to one more and they said you can't come back anymore you're not you're not part of the yeah part of the the ceos anymore i didn't i got i got i was off the team and you know ben chestnut did an interview just a couple weeks ago with klein perkins and said the biggest issue when he sold mailchimp for twelve billionaire or whatever it was is was he knew he would be instantly irrelevant he knew he would be instantly irrelevant and he said i am now i'm irrelevant now mailchimp of the past he's like you wouldn't even build it tool a like mailchimp today in the age of ai right maybe that wasn't quite at the point so yeah so so that was it and then but then what was fun for me and this is is a long time ago but what was fun for me is because i was the first of those ceos like the errands and the david's sachs that had an exit i didn't have to pretend anymore so i just maybe sam thought i was grumpy but i just shared every mistake i made how i screwed up my first vp of sales how i screwed up meeting customers in person how i screwed up marketing and there wasn't much content back it's a little different than today there wasn't much content so everyone to start to read this were you being strategic you're like oh i'm gonna start doing content marketing that's gonna lead to this to leave to this are you're just like i've got time on my hands i got stuff to say i wanna start blogging i did what now people give advice to but i didn't there was no one to give the advice i just wrote one blog post a today on a mistake i made that was my my paradigm right a mistake i made as a b b founder that got to tens of millions and back when cora was a platform and people listen to this one won't even know what it is but sam samuel well i answered one question i answered one question so peep this was a way for people to ask me questions and they those were great because they were very tactical right they were very specific so i would do one a day every day and it it does you know i'm a it's a little different today in ai but generally speaking if you do that it compounds right it doesn't compound the same way revenue does but if you do my first million every week and you just keep working at it and you it does seem to compound doesn't it just not not quite as literally as we might hope but it does compound but i didn't know one there was no advice back that i just did one one in one a day you're also one of the first people to do twitter you're one of the first like tech people to like you know for a lot of tech people twitter didn't boom until covid but you were doing it very early you know it was like and gary van vaynerchuk twitter started with tech what do you mean i don't think it was taken seriously i think that i think jason looked at it as a craft where he was like i'm gonna a girl huge audience here i i think sean that for a long time twitter was an afterthought to a bunch of different social media platforms now i think it's bumping i just think i approach it as a micro blog which is what twitter in the old day's called it so i would put valuable content on twitter instead of being g or just just just you know peep and so i was early to putting valuable content i think on twitter right i think if i benefited anything in content i think it was just being early you were early you've been dude you are an output machine and the stuff that you write about is lyric like you write about thing saas is a stupid boring thing you write about stuff where i'm like i don't even own a software company but i wanna i love reading what he's you know it's head of like die work wear with clothing it's like you don't have to know about clothing but when he talked about ties for some reason it's kind of exciting well that's a good insight my actual real goal of doing it was to make it more fun building boring business software make it more fun not not not in joke way but to celebrate the fun part the exciting parts of it right that that that was my version of what sam said did you think okay then i'm gonna be investing this will help with deal flow and like where did the conference coming in because that's a kit pretty gang business i can't imagine you thought at the beginning we're gonna be doing five million dollars per employee we're gonna do twenty five million dollars a year in this business where we have kind of like a little like our monopoly we're the big fish in this small pond of of of basically like thought leadership for saas businesses well the pond there's more thought leaders today but if you if i mean it's a while ago but if you are curious i just wrote this just because i was a blue and it was something to do something to share something to add value to the world right no goals no goals i certainly wouldn't start off with a blog today if i start off today right is as archaic it is they're still is seo but what what would you do even it's not me right but of course i would do video i do video but i'm not you got like it's not my natural i'm a good writer i'm not like a or ernest his tell me but like sam said i have something special i'm able to convey ideas in a way that helps people in writing and i still think today that's a rare skill right did i hate video sean's pretty good at it sean i can talk to a camera by himself and in six seed i hate it i hate video i think that like i think there's a generational gap need to put a like the super cut of sam's ad reads oh my god they sam talk dude ad reads it sucks man i i it's not i i'm incredibly uncomfortable doing it i think but i think that like the twenty five year old today just like the fact that facetime has existed there's so much better at it so there's like a huge there's a generational gap but i'm like four years to old two have i've caught but if it's of interest it might not be the investing was an accident too it was an accident i actually for about a little less than two years i worked at a vc firm that had invested in me so they they recruited me to help them i had no real interest in investing and i showed up and i like i don't know what the hell like this is not me i don't know what to do here but luckily i started this blog and founder started to come by the office so first the founders of pipe drive came by the week i started and that was my first investment that's sold for billion and a half right then other founder started then founder of talk test came by that one was worth ten billion this last round then the founder goalie came by that's worth two and half billion then the founder of sales off came by we sold that for two point three billion cash in twenty twenty one and they get kept coming by and i'd be like well let's just invest in these ones because this is the best ideas i got like i'm not the outbound guy like fuck and say i'm home and i just invested in the five best guys that came by the office the first year but they're all worth ended up being worth a billion dollars so so that's i i own so the weird thing about me for investing and then i could tell you about events real i almost spend time i only i'm i'm different than ninety nine point nine percent of investors i only do faster super fans that are high intent inbound i don't take favorite meetings i don't do warm intros if you tell me sean there's a startup up that you want me to meet to invest in or understand i would ask is this do do they desperately want me and they'd be like no they haven't heard disaster him out right but if they really want me they probably just email me so i don't even wanna warm me intro i don't even want it damn mormon joe that sounds like such a leak in your game by the way that sounds like an unnecessary bar right like not only if i get a warm intro that they say this person's kick ass and they'd loved you know but it's like are they a huge fan if they're not a huge fan i'm amount that that just the thing is like investing so much harder than it looks the odds that any start like seed start gonna truly be worth billions of dollars is much lower than it looks on the media it's really hard and if you don't have like if you're not incredibly intense if you're not incredible if you don't want this more than life you're not you're gonna you're just gonna sell your lifestyle business which is very logical right oh so you're basically saying if they're not like basically digging my content they're not taking as seriously as they should is that is that the implication basically that if somebody is seriously trying to build a generational company they should be loving our content and therefore they should want me on the cap team i want them sending me a cold email that is so good that you would invest off the cold email this is how invest i want a cold email that is so good that is so good that you don't even you almost don't even need to meet them the only point of the meeting is confirming that you wanna invest like every investment i've done that's good i've wanted to invest before the meeting every good outcome i had this how i invest in in owner i'm a little bit after you guys but i got an intro that was like this guy's one of the best founders i've ever met and ever invested in and this this company is growing incredibly fast yeah and then he sent a cold email basically they right after that which is like hey here's why i want you on board and here's my last three investor updates and in that one of the things that he shared was they had done like a hack week so there was like some loom videos of the team sharing their hack week projects and i actually just watched those yeah and it just show like the the caliber of the team was really incredible like you can see the caliber team in a hack week project right almost by definition here's just like one an engineer and a designer they come up with their own idea they have a very short timeline to ship it and then they have to pitch it and present it so you get to see like the the quality of idea the quality of speed of execution and the quality of salesman all in one from like without abstract away the founder it's like that's the team itself and i emailed him back with you know i was like we don't need to meet i'm in yeah you that's it's not the only way to invest but but i can tell you is if the emails mediocre they're not gonna make it there are exceptions okay i know there's exceptions but man wait to dude so we just at hampton we're hiring a bunch and i'm putting together like values to look for when hiring yeah and i only made it i think i'm only gonna to keep it at like two or three values but ability to write in the email and communicate is the is one of the three and i will tell you of the re one of the reasons we only have the five people is i have lowered the bar at sas in a way i never would as a software founder i've lowered the bar again it again i've hired folks for the email wasn't that great i've hired folks where they put an e faster i've hired folks that didn't do the research before they started hundred percent failure rate hundred like we already know this right but i've i've lowered the bar because i'd be like well this isn't as cool cool enough what i gotta take who i can get right all always a neck worth less than zero right total was total zero yeah you have this great tweet you said you think startups are about a great idea but in the end they're about great recruiting that's what you're talking about they they yeah and if you talk about own or not to use one but because mutual i will say there there actually a lot are lots of risks with owner and i invested very early you didn't see the two times we almost ran out of money now we have infinite capital a lot of other things but i actually do not know a more relentless recruiter than adam i don't know a more relentless recruiter than adam and that that is a rare skill we all learn it as as theo like we get bet we always get better at recruiting right what does the relentless look like like what is literally reach out to the two hundred best people in the job talk to all of them set up means cold warm lukewarm direct linkedin who are the two hundred like talk to everyone who are the two hundred best cmos that i could possibly hire don't pretend to talk to two hundred don't actually only do five interviews and pretend you're doing them do two hundred that's what the s tier recruiters do right the s here i had an old cofounder and i wish we'd gotten along better but he was one the one of the best ever and i'd roll into work every day at at eight o'clock and he'd already handed me two candidates to talk to that were really good every day every day i've never adam has that but i've never seen that magic right and i don't have that skill to every day he'd found a way hey i've got this marketing and the sales guy wants you to meet can you talk to them today be like two more but then they'd always be great they they're not they wouldn't always be a fit right and that's that's how only way you can scale as an executive unless you have a three person startup up you have a few more of these really great like how to be a great ceo concepts so one is to be a great great ceo you have to enjoy telling the same stories again and again and again hundreds of times yeah yeah even sam alt does that doesn't he it's pretty much the same story right it it it it is that that one the what i like that sam does is i can comment he tells you the future like elon musk if you're listening so do you mean by that well you know he does this you can make fun of this goofy video he did with johnny iv i don't know if you saw it when they did it like perfect let's having coffee in north beach my favorite rom come of the year i yeah you think oh this is silly right but but listen to what he's saying he's telling you that in the not distant future you will be on chat she twenty four hours a day right and i'm making the bet that johnny iv is the guy to do it i'm not betting that he's gonna build a rabbit pendant it's not that i'm making a big bet that he knows ui and ux so well the next generation that he will solve this problem where we are on and sam already on chat eb more than the average today right the average person's on like twenty two minutes said you're out it more aren't you i'm on it all day yeah so johnny iv i is gonna figure out a way that it's in your ring and it's in your phone and it's in your glasses like ray band and it's gonna figure out stuff we haven't figured it out and it's in our it's in sean headset and we are just like what if it was in this headset like this is totally passive right i mean i don't know if you guys have used granola or the newest notion it records everything you do all the time in the background without permissions or visibility you know why granola is so successful by for note taking versus i don't know if the one you said is does this sean but i you know granola just records everything at the hardware level like i could be recording us an renewal right at all and you we had we had we had a chief customer office officer summit three two hundred of the best chief customer officers it's disaster this year and the guy that put it on that day wrote up the whole summary of every single session that day like very very good i even i couldn't do this it's like i just granola just listened to everything and wrote it for me and it was done that day do you feel this way sean where i hear this and i'm like this is so exciting and then but the other side of me is says this is so intense i to like i hopefully i can invest in something and and make a profit oh otherwise i need to take my weddings and go home and hopefully they compound compound by themselves because there's an intense feature that you're painting here like i i don't know how i feel i sometimes i'm like this so exciting wanna again this is this is amazing but in other times i'm like if my life depends on this i don't wanna play this game so this seems so intense i do exactly what you mean i've i've now experienced basically like i graduated twenty ten right so when i graduated i basically like that's when the light bulb turned on i don't don't i don't even remember life really before that know i i didn't even know the great financial crisis was happening i was sitting at a chick f a somewhere in o eight you know i i just was used to to the to the whole world right so when i came out twenty ten basically three things have happened since then that were of note there was mobile so right when i moved to san francisco i remember we you i joined bur startup studio and there was a single mobile developer and he went the by my very first day he was giving a tutorial to the other twelve engineers were like you know super seasoned silicon valley engineers but they just never built an ios app before yeah and and like that ratio of like one mobile developer to you know fifth twelve fifteen non mobile developers within twelve months at flipped it was like if you're not doing mobile what are you even doing why would you do a startup it's not a mobile startup up it was like a a a dumb idea and by the time you're you know a year later into the job and so i saw mobile come and mobile was one of those where i would say it was obviously going to happen but it was a fog of war you didn't know where the opportunities were if and actually the opportunities were very different than the previous wave so like michael who had made a billion dollars in web one point o or two point or whatever like you know the facebook era he didn't realize even facebook didn't realize z didn't build mobile apps right he was like no it'll be mobile web responsive that'll work and you know the fact that basically uber was like the big uber was like the biggest winner basically during that like that era when we when we launched and uber was like physical world interaction he you pushed a button but a car has to show up and you have to manage these drivers and that looked nothing like the winners before so there was like we all knew mobile was big but we didn't understand the the fog of war prevented us from seeing the path to victory yeah then the next one was crypto crypto had a different flavor which was it it was not consensus that this was gonna be big fact it was very fringe and you looked a little crazy for saying this was gonna be big and so most of us missed it for that reason and now this is the really the third one i'll like take covid out because i was that was at a little bit of different thing this is the third one where again everybody agrees this is gonna be huge this is gonna be the biggest of all of them is the biggest opportunity ever right so everybody agrees on that but there's complete fog of war because like you're saying even the apps that are working get disrupted the so much creative destruction layers disrupts one moment you think it's the models that are gonna get all the money then you think it's nvidia that's gonna get all the money then you think it's the applications that are gonna get all the money nobody knows how to win even on the investment side like the vcs also you're sitting there and you have this really weird feeling because you know this is the time when all the money gonna get made the generational money is gonna get made now you still have no idea where to put it and people are trying to figure that out in the fog of war it's like that warren buffett phrase where they where he says every every you see who's something naked when the tide comes in or goes out you what i'm saying where the the idea being like you know when there's turmoil that's when you get greedy but the hard part is a the courage and b to know when the turmoil is actually happening you know are you in that period now we all know it's happening this is the time but do you or i have the want desire courage to actually get after it and half the time i think hell yeah this is amazing the other half of time i think this is this is scary i don't wanna read a book yeah i want nothing to do with you know what you do you guys agree was i wish i knew it was someone on twitter had a good tweet that resonated with me on this he's like what the the smartest display if you can possibly pull it off today is to go make five or ten million cash out and just chill because you can't protect where it's gonna go like this is the world's gonna be like whatever you could do to to liquidate your assets now they may be worthless down the road so liquidate them right now in chill if you don't if you don't see the future because this is the time right i and i do think and i also think you know i used to it it it wasn't until we ran our own ai again i used to think the node c i mean obviously off the charts smart right but when i used to talk about how ai was gonna bring mass unemployment and tech i used to think he was just being crazy right but now i can see it it's also coming i can see all the maybe kin just laid ten percent of their their team off but it's just a start because they put in all of their learnings all of their data into their own ai like faster and now they just ask they they don't need the kid anymore right half of our sales and marketing teams are gonna be gone in two years there will be no bd in a year and so this mass change and it it is hard to make bets so what's happening in venture for what it's worth there's really two things happening right now in venture seventy percent of the money's is going to growth and right now it's a great play you do claude at a billion and then it goes to three billion and the valuation goes five you put in two hundred million that two hundred million goes to six hundred million right you take home twenty percent of the profits you make eighty million dollars in a year right that's where venture going all growth it's all growth and then it's doing seed early stuff but implicitly people are assuming a very high loss rate and they're paying very high prices sixty million hundred million dollar valuations at seed and they're hoping it's worth billions but they understand like there will be uniquely high loss rates too they're not saying it but they know it right they know it yeah and that seems hard to make money right those two that combination of high valuations and high loss rate that doesn't you have a hundred billion dollar outcomes if you get one per fund all that that's the bet they're making that there'll be one hundred billion dollar outcome for each venture fund right but back when hubs again when hubspot ipo the bet was you'd have a billion dollar outcome per fund one right now it's hundred billion per fund so if you believe you'll do that you can do some you can do a little analysis or waterfall you just guys have claude do it for you you don't even have to do the analysis yourself anymore i did this over the weekend you just gotta find one of them and they all the rest can crash and burn right so what is your game plan i have decided that whatever brand i still have and my excitement and my ability actually to know more than because i've done my ai actually know more than most people that aren't that aren't on the like programming tool side i've decided that i'll get one at least one ten billion dollar deal done in the next three years two years one no matter i'll i'm only in it for one whether that means i to do twenty investments or one more it doesn't matter i i've in it for one right at the seats at the earliest day i wanna own i wanna try to get one deal where i own ten percent or close that's worth ten billion i've sort of done it once on paper i've done a couple billion dollar ones and i'm and i've missed a lot what would that be worth to you if you own ten percent at seed of a company that's outcomes at ten billion well multiply if it's just ten if it's just only ten billion that's it but multiply it by ten percent so that's a billion right and then you keep twenty or twenty five percent of that dilution lot you right so i'm asking you don't account for dilution no i'm simplifying my goal you could own more like you'll own more and then there'll be investments that are highly at a add a ten billion dollar outcome at a seed stage you are looking to make two hundred billion dollars yeah that would help okay that'd would be cool yeah i think listen if you really wanna know how venture if you really want i i know we're going enough to talk it there's two ways that i think venture works if you wanna simplify a lot of it one it's a great job one it could be a mediocre job it could be a great job or you could try to make at least a hundred million dollars i think anything else is it doesn't exist the gap there's a gap it doesn't exist because you're either in it for the fees and the job like initially like wow i'm a kid i'm getting paid two hundred fifty thousand dollars and i just get to take meetings it seems great then you're finally a partner and you make a couple million bucks a year and that's like much better than like some other job but there's a pretty big gap between that like you don't it's really actually unless you're great it's really hard to make profits and venture carry so the game is to make a fucking lot of it okay and listen and the thing is if you're in a big winner if you're in multiple big winners just do the math sam like that's why most vcs make nothing except a good salary but there are a bunch that have made billions because if you're in like three or four or five of those ten billion dollar outcomes which is very hard then you make a billion bucks now the founders hopefully make much more it it is fair right but you're either playing that game or it's a performative of game or it's really just for fees and salary like there really isn't a there's nothing in between but you also have the media events business too so you also have this cash flow i assume that that's a very profitable business it wasn't before covid but it is now yeah so you you have that either way yeah i mean i made enough as a founder i have a safety net i mean but i don't i actually view it as a net negative for investing but it is but it's a passion we we do a good job but yes last question i i know you have college age kids freshman sophomore yeah what are you advising they're gonna do when when they're saying dad you know what should i do for a job if they if they ask you that what would you advise them to do now first i i i don't think a lot of these kids will ever have a real job they'll find ways on the internet to make my so so i'd it is interesting there does appear to be a a gender difference which i don't like between boys and girls of my son's my son's a sophomore now ten percent of this class didn't even wanna go to college at all and they just decided that they could they all had this five i'm gonna go to eastern europe or it's cheap and i can just make money on the internet i'm never gonna have a real job there's no interest in ever happened and i don't think my son really wants to ever have a real job and he's super smart like he's much smarter than me math he's now into he's deep in ai he can he's deep into cursor and win serve he pays for cursor out his own pocket he's running assembly language now so he can code to the metal and do everything but he'll never have a real job okay he's like worst case i'll work for airbnb b from right yep so he's never gonna have a normal job ever okay by daughter it's interesting she's at stanford okay and the vibe at stanford this is if you ask it's kind of interesting this is a shocker to me they all wanna go to grad school now as freshman so they're all they're all architect their classes their majors so then go to grad school so they can defer work like when i was in college people cared about grad school then i think people made fun of grad like why would you go go to grad like why would you go to school i go get go go to the internet right that was the vibe for for fifteen years now they all wanna defer reality and i don't i don't know that there'll be any any jobs and i don't know that people wanna work i honestly don't think and i don't mean this negatively i don't think a lot of the current they wanna be creators or they wanna do other things i just whatever made us wanna work the three of us i don't see it in the next generation very rare the women wanna be educated and the men wanna move to eastern europe and make i'm not sure it's the women wanna be educated i just know her group does that may not the men not wanting to work at all like like coming out of high school and just saying no fear like no fear i don't know when it was like you when i during my life i was worried i wouldn't have a job at different times right i was worried during college i wouldn't during i was always worried there's no was i was a senior in college i remember thinking man i would kill or k g and make forty five thousand dollars a year like i i i i remember they thinking like that would be a home run if i could senior your year book quote i'm like pay p g in nashville national tennessee if i could be if i could get fifty g's from deloitte that's a home run but it's so so i think i don't know that they're gonna work and then i think a lot of the twenty twenty one generation isn't going to work again either i'll give you an example so someone i knew a little bit there's a lot so i've i did this exercise i just like lowering the bar for hiring i did this exercise i know i shouldn't it but i wanna try anyway i reached out to folks that had that the circle in linkedin what's the circle on linkedin out of work what's the called looking for work or like yeah open to work i looked i worked out to folks that i knew a hint of i maybe i met them backstage at a hustle event or something i i i i met them in passing okay enough that i had like a micro connection that had been out of work for six months and i gave them jobs all of them in the end basically said i wanna make two hundred care more only to do meetings or manage teams none of them are willing to do any work themselves none of them through young people the gen z's open to deserve their ethnic their their expectations for salary or for comp is so high well there's that like i'm talking about folks that are already bid out of the workforce for six months but yeah expectations are they'd rather not work that's the thing a lot of people would rather not work than get their comp right i mean yeah that sounds good to me too i don't know how everyone's like listen there's obviously an element of privilege in this right and for folks that are living in different geographies or others will think this is disgusting and i think they're right but i also think folks who have made a little bit of money in tech or otherwise are happy to live on relatively low amounts of money with with their savings or others rather than just take a job no matter what it's what what the internet says right jason is this a stupid mental model i do this sometimes if i if i wanna hire somebody and i'm interested in they're two hundred thousand dollars a year let's say yeah and let's say my business is twenty percent net profit margins i think to myself this person has to basically generate a million dollars of extra revenue just for me to break even on their salary now maybe they're maybe they're doing it in coordination with a team but like the addition of this person in order for it to be a positive roi i have to believe that adding this person yields me a million dollars of extra revenue and when i do that i mean ninety percent of the i'm like there's no chance no this is like that that wouldn't even make sense here so i don't know if my mental model is broken or if i'm actually on something with that is that how is that is that a really dumb way to thinking about that that is that is the model for sales reps like traditionally a sales executive whether they sold software or an automobile a sales executive in base bonus would take them twenty percent of the profits if you look at how car dealers car dealers have low margins right but if you look at the margin to a car dealer that the the guy selling you the the new the new lexus net net would take them twenty percent of the profit to the dealer right if the dealer made no profit they'd beg nothing if they ripped you off and got you to pay list plus the the cd player for a thousand dollars they'd make a lot right sales is the same way because in in in software the margins are almost a hundred percent reps would traditionally take home twenty to twenty five percent of what they closed right sales for other roles it it's really just about leverage and you're often just hoping to break even but even to breakeven even let's say it's a two hundred thousand dollar employee to breakeven even you need a million dollars of incremental revenue to break even on that yes but one way this is what i learned for example one way that law firms traditionally were structured it this is slightly interesting and it may be different today but traditionally law firms actually most law firms not the big the not the lit but like your corporate law firm that helps you on stuff they never made money on the associates okay so why would you have associates i didn't know this till i asked a partner that i work with doctor he's like because i just don't wanna do that work anymore i don't wanna write the certificate of corporation for sam i don't wanna do the nda like i don't we don't make any money net net of training and off boarding and churn and the and the desk and the computer we don't make it but i just don't wanna do the work so your organization you'll also like just to not have to do the work right but the problem with ai is it lets us do more of the work that's the weird dislocation so instead of paying that person like you can't even find the two hundred thousand person dollar person at some point you'll just do the work yourself with ai right that's the cognitive load but that's why it's a mix i don't think everyone can be profitable some folks just have to reduce the load on everybody else but ai is gonna do more of it yeah right you're full of information i you know i think theo von described one of his guests as a blind russell terrier or jack terrier or no sorry a jet a death a what was it a deaf fucking ruin this joke but where you know what anyway boy is it got a def a deaf jack russell terrier where he like gets out of the of the car like goes crazy to kick stop him from y yeah that's kinda like what you are where it's like we just like hit record and we just like you just roll and we just are on on board and listen to you and you're the man you you're just full of i think really good comments that are done in like strong taste and tend to be right jason don't get confused when he calls you a a blind deaf dog that's he's trying to give you a compliment that's just he does a little bit differently yeah yeah and grumpy yeah and he goes to grumpy so you're welcome and welcome to the show there's a good bag for you on the way out thanks man you're the best that's it that's a pod i feel like i could rule to where i know i could be what i want to put at all in and like a days off on a travel have a look back