#167 - Answering Your Questions On Investments, Businesses and Life

you would know more than i am but this guy is tim and his brother i i'm not that close with them i'm friendly with them i'm friends with them but i'm not that close like if you told me that they were worth over a hundred and fifty million dollars i wouldn't be surprised if they still ask like they're poor in in kind of a funny way which i enjoy and they're they super humble and they're like super horrible and they invest in everything yeah i feel like i could rude hell i know why i could be what i want to from at all in it like a days off on a road less travel never looking back today we're gonna answer a bunch of questions but did you see trunks tweet about the guy selling the card no what is it t tweeted out this video that he found from probably the nineties or probably from the two thousands early two thousands and it's a guy who's got like who's like trying to sell you on his like business card that's a big square and you open it up and it's a pop out and he's just really intense but the video got it it's funny you haven't seen this no oh well this won't be any good then but the video got like half a million views and people are making websites about the tweet or about the video based office we it was just funny it do you seem to million views now or like he tweeted something that already had half a million views no it did now oh wow t is a master of finding great content that guy is really good i have this like apprentice who's working with me chris for content he's guy yeah yeah yeah he's like kinda like shadowing me and he helps me produce my content and and he's learning as he goes and i told him i was like you know success is being trunk so like that's the level that's the top bar that's that's what you need to measure against here's five examples of like awesome things he's done and so he called trunk and he was like what's your secret what's your process basically truck was like you know like i kinda browse the internet a lot you know there's no way you can you know it's like i asking michael jordan how do you jump so high type of thing like it's not it's not easy to describe how you do the thing that doesn't feel like a real process for you you know you're just doing it native intuitively he's a machine one time i called him at eleven o'clock his time he's in vancouver and he was at the park playing with his son and i was like trunk like i'm not trying to like get on because i'm not your boss but like don't she have work to do he was like and he was like bro i wrote i got up at five am but i already wrote tomorrow's email already was like alright sounds good okay he's a machine i didn't see this video is is worth talking about given that i didn't see it or what it's too long to go people and myself let's go to twitter after this said let's go to tron t fan i think this is is a handle and yeah look at his thing and he the funniest thing that he's done lately is he owns only fans dot com dude that sc me it was so funny so he has only fans but he spells fans p h a n like his last name and it's just a network for only people with the last name fan and i just thought so funny oh was and for some reason it's funnier when i think that he came up with the for you yeah now we don't like it so much stupid joe super exciting to you alright so they hope we're gonna answer questions i we got it looks like we've got like six pages of text questions so like dozens of dozens of text questions and then we got a few dozen audio questions like people calling in but some of the text questions were good i'm gonna start off i'm gonna start i'm gonna read a few you that i think are cool let's do the first one this guy's name is johnny vol what are you both personally investing in right now by like do you wanna know johnny v do you know who this is he i talked to him on twitter and he's joe spy buddy he lives out here in the bay he lives like i know fifteen minutes away for me he super successful e commerce guy in an e comm for ten years sold his company recently like i don't know a month ago or something for tens of millions of dollars and is he's a big investor in my rolling fund and several other the rolling funds and really like ultra nice guy so this guy is super legit so he's asking what are you both personally investing and so you wanna go first i think you yeah i think your your answer is probably more interesting i'll go first so right now the bulk of my liquid net worth is in publicly traded companies i own a bunch of hubspot right now i own a bunch of airbnb besides that i don't own anything else above fifty thousand dollars the it's all in so you're super concentrated in those two companies basically yeah but then i have more money in the s and p five hundred so there's like the total stock market index i have i'm i'm gonna invest around two hundred fifty to five hundred thousand dollars in the next probably eighteen months in startups i have i own six figures worth of into a variety of real estate funds including sweaty start vancouver and then i own my house and i'm in the process of buying multi family properties so i would say i have like if you just broke it out you're like per you know roughly you're like okay seventy percent is in the stock market really in the two companies you know where where my wife works and when i work something like that no i i own way more just s p five hundred than i do hubspot and airbnb but i would say that ninety percent of my net worth is in the s five hundred yeah oh wow that's me okay so just like low low low cost index fund basically vanguard fund simple stuff and then my goal is to invest somewhere around one to three percent by net worth over a period of time into angel investments gotcha cool and then some real estate mixed in real estate being you know the house you live in and some other you know projects other people are doing you you're not currently buying and like owning real estate at the moment i'm going i owe my house but i'm i'm gonna i wanna buy sixteen units i also have i mean i'll say like half a million dollars in cash just sitting in a checking account which i think is too much money but i when i bought my car i just paid cash out of there and then i i owned six figures of bitcoin and ethereum of which i owned most of that bitcoin from two thousand and thirteen and i just bought like seventy five thousand dollars for the big ethereum like a few days ago because you and a few others told me it was interesting nice by the way we got some criticism constructive criticism i would say which was like oh last few episodes feel like you know rich guys talking about you know ways to make a bunch of money which honestly good description for the podcast but but i i get what the person saying because they're like a fan and they're like i that's me raising my hand because i think i basically was like oh this big clap thing is cool and it sounds like a total po scheme and so people are like what do you or we're talking about like jack selling like a n for like seventy million dollars so it just sounds like a little bit crazy so i think you know although i think your answer is great because i like knowing how people invest their money i think it's most people are very closely guarded with that info people don't tell you what the hell they're doing so you're kind of on your own to figure stuff out and you don't really have any data points triangulate because all the wealthy people don't wanna talk about what they're doing with their wealth unless it's with other really wealthy people and so i think it's great you said that but i'm also as you're were saying it that was just ringing in my head of like some guy like why you guys just talking about money but it's like well that's also the theme of the podcast in a way and that was also the question i'm trying to answer it truthfully but also when we started this podcast when you started this podcast a year and a half ago or two years ago it really wasn't as a bunch of rich guys talking about it was a bunch of hopefully soon to be rich guys talking about stuff if we've been talking about the same stuff the whole time yeah oh you mean us yeah that's point yeah because yeah and also i put this out there in the manifesto when i started this thing which is i i think it's unfortunate that talking about money and how to make money and what you do with money to make how you make your money more earn you more money i feel like it's unfortunate that that's taboo to talk about like it's like kind of like a it's like kind of like low class or something to talk about because look the reality is most people want more money and people try to signal and say oh just matter and all this stuff i know a lot of people that want more money most of people in my life if i had the option would you like more salary or less would you like more in your bank account or less like the answer is more and if if all the people who have money are really guarded and don't talk about it and don't wanna seem like they're bragging well what that really does is it kind of like just traps the information from others so that's kinda like my my overall view of it i know you're similar because i remember being kinda stunned when we first became friends and you just facebook messaged me you're like like how much do you make i was like whoa whoa bro like what's going on here but i was like okay you know balls question the reason why that i actually dislike that view that's or if someone criticized you ton about money it's because they are making the assumption that because you have money or because you don't you are somehow better or worse and in my opinion like i don't just because you have money i i i that's you have no intrinsic value to me like you either are interesting or you are not interesting and what makes you interesting to me is that people are just they try ambitious stuff and they do need stuff oftentimes that's correlated with money but it's not always like i knew this lady who would do these amazing art exhibits where she would like paint gold phones and like just do interesting stuff i was like that's super bad ass that's so bold of you to try that she wasn't wealthy at all but i thought it was so cool right so to me it's about just being an interesting person i don't really care if it's money related or not but oftentimes it is right for me i have like three or four different life games that i'm very interested in like let's say right now i'm interested in the fitness game and i'm a total beginner i'm a white belt at the fitness game and so i have a trainer he's like more like a black belt you know look at his body look at his lifestyle he's extremely healthy and so i wanna learn about the fitness game i like learning about the happiness game how do you be a like a happy person how you control your mood how do i master my mood i'm really interested in that i think about that a lot talk to people about that then there's like the money game and then there's like the making things that people want game and i like all these games and i admire the people who have done well in them and i'm better at some than others where i'm like a total beginner and then some i'm like you know a blue belt or a purple belt where i've done something but i'm by no means at the end anyway that's a tangent but to answer john's question did you wanna say something else about that no i answer to to answer john's question i'm kinda similar i i i tweeted out my like holdings a while back i maybe do that again i i need to go back and recalculate but i tend to hold about ten percent of my wealth in cash i think cash is being dev and i don't wanna hold cash cash doesn't earn you know cash i thing in the bank is nice for a rainy day but it doesn't earn you more money right the point o zero one percent i get from wells fargo or whoever is not gonna like help me i have a good size stock you know basically i would say beyond that it's almost like fifty fifty of public equities so stocks and you know crypto right now and i and and then angel investing so i'm angel investing currently through the rolling fund four million dollars a year but that's not my money that's mostly other people's money and i get a carry on that i get a twenty percent carry of the profits so that's kind of like investing but i'm not investing my own money there and i'm looking at real estate right now but the problem with real estate for me is has always been a i'm a beginner at that game and b i don't wanna sign up for more work so i'm looking for ways to get real estate that's i directly own but i don't have to do a ton of work and those two are kind of at opposites with other i don't invest in other people's real estate funds right now has your net worth or like your total portfolio increase a significant amount since your deal because it seems like you've like weren't very active before and now you are very active and has that helped you it has increased because you know the stocks stock market's been doing amazing last few years and then with a deal you know like where we when we got bought the amazon stock price was eighteen fifty amazon stock price today is thirty one hundred so just while working there you know you could get pretty significant gain in your holdings there and because we got bought like a large chunk of the rs asus were just in that one company so that did well crypto is bitcoin has done extremely ethereum has done extremely so those have like really worked and then kinda like the side hustle money from podcast email newsletter stuff like that sponsorships that that sort of thing has been really nice so that that's that's actually picked up as well where i wasn't doing that before so i'd a yeah but i would also say what really changed was my attitude like i just started acting like a guy who's got a hundred million bucks for better and for worse like i take like bets that are kind of too big for my bank role sometimes and that's a risk and i you know i might pay the price but i sort of just started carrying myself and acting like and basically making decisions like what if i wasn't worried about money what if i wasn't worried about you know going from a to b you know like what if i just knew that i'll get to be pretty much regardless so how would i bet if that was the case and so i started making slightly larger bets and just being more active whereas before i was a little more conservative with how i was investing which is a huge difference in our philosophies i'm way more conservative than you way more conservative yeah and i don't think i was telling bra you he was like because i told him i start angel investment who's was like who you think it's gonna have a better portfolio and i was like that's kind of interesting and i and the answer was like my answer to him was i think my portfolio has a higher chance of being pretty good whereas sean's portfolio has a higher chance of being amazing or zero right yeah that's true that's that's definitely true i i guess like the style of who you admire sort of dictates what you did you like what blueprint you create so like for example i was really inspired by like chris approach to how he went from like you know he's like me he's like a bit of a degenerate gamble like he went you know he took like his law school money and then like was day trading in the stock market during the dot com boom wrote it up to like a ten million like took twenty five thousand and turned into like ten million dollars and then went into whole four million dollars like that was like a crazy degenerate gambling run if you haven't heard me talking about my bets in crypto and you know i used to play poker like i'm obviously i have a gambling problem also right and so you know i have that risk and reward profile but then the other thing he did that i thought i i was pretty inspired by i was he you he bet on somebody he who he believed in which was evan williams when he started what became twitter and then when he saw that it was a winner he like went all in in a way that most people do not most people would let their twenty five k checks sit and been really excited and fingers crossed i hope twitter becomes a thing he likes started to quit he quit his job basically started showing up at the office every day being like how are we gonna make this thing grow i want this thing to grow he went and personally was fundraising for the company even though he wasn't even a part of the company but he was out there pitching investors to invest in twitter and then he ended up buying billions of dollars of twitter stock before it went ipo and was theirs i think first or second largest shareholder at ipo and made billions of dollars off of his twitter holdings because he knew when you have a winner you gotta go all in so what i've seen is in technology the winners get really really big and so you kinda wanna like play small bets initially and then follow on really hard and like when you see something that actually works be really bold in the way you approach it and like hey if you strike out like i i kinda just think about it like this i have a lot of faith in my skills even if i went to zero today i think at three years i'd be right back where i wanna be where right back where i am today so like i don't feel like there's a huge risk in terms of that but anyways that's a little bit off topic for one question alright let's do the next one which was a question that i actually have for you as well update us on your rolling front fund is it what you expected are you more or less bullish on it it is not what i expected in that i didn't really think too much about it before i started it to be honest which is you know i'm kind of i was just like oh yeah that sounds like a cool idea let me try it and see what happens but i thought okay i already angel invest of this is just gonna be that with some bigger checks or you know do a few more deals but i would say now that i have to deploy a million dollars a quarter i actually have to carve out more time i have to like consciously go and invest in more company so it's a it's more work than i thought initially but i brought on rom and i brought on zach ben helps me with it and so they do a lot of the heavy lifting like for this week's this this year's yc batch you know zach himself referred in twenty two of the companies he was the number one i think referred into yc so he knew a bunch of the yc companies before they even got in we looked at those deals and then rom romaine basically and ham went through every single deal in an air table vetted them made a list of the interesting industry wants did meetings with them and then brought the like most interesting seven to me and we're like hey we think these are the ones to do and so that that like i've been able to handle the additional so it's more work than i thought but i found really good people so that's helpful who's this guy zach zach is a young engineer he was a yc founder himself that company didn't work out he currently so so i met him because he listens to the pod i don't know i don't know how we reached out but he's like hey heard her think about rolling fund i'd love to help i just wanna see a bunch of startups and help a bunch of founders while i think of my next thing and and it just turns out he's just like super well connected with the like young founder community and so because of that he's like referred a huge number of people into yc and into on deck and so he's got his really great network and he's like able to like see things earlier than most and so i brought him into the fund and and gave him a chance to hey now you can have some upside in this in this thing that's bad ass and then are you more bullish or less more yeah like the same i don't know i was i have a friend we have a mutual friend su who he wanted to get involved in a business of mine and he goes he said he texted me something because i was like i was like kinda i don't know is this i don't wanna give up equity but like you know i think your comp thing you're worth it yeah so so basically he goes he goes look if i try i win and with this i'll try and and so i just loved it i was like i've i've just gotta learn a lot from these guy's philosophy and business he just has zero of the doubt and fur and i think that's experience you would know more than i am but this guy's tu and his brother i i'm not that close with them i'm friendly with them i'm friends with them but i'm not that close like i if you told me that they were worth over a hundred fifty million dollars i wouldn't be surprised if they still act like they're poor in a in kind of a funny way which i enjoy and they're they super humble and they're like super horrible still julie is silly super humble yeah and they invest in everything so these guys are interesting they're two brothers yeah and and so the same way actually when i first met him i met him at you you hosted the hustle content at my office this is how crazy the world works this is like one of those you can't connect the dots looking forward you can only connect them when you look back you reached you cole emailed me saying hey i wanna host a a dinner at your office i didn't know who the who the hell you were but you made a strong pitch you said i'm gonna have all my speakers from my conference there you can you can ming you know meet all of them i was like alright fair deal you can use my office at that dinner i made sue so he's now my best friend we've done tons of deals together you know like that wouldn't have happened if i hadn't said yes to something that was kind of a random thing that's fine at that dinner i was like dude this guy's amazing i've never heard this guy's name before why don't people silicon looking can barely know this guy so i started googling them i find the story that back in the day he sold his he he had this company that was like building facebook apps and he sold it for not a ton of money but like you know good for any normal person like two billion or three million dollars between one and three million dollars kind of what it sounded like and and so and then what did he do with the money he was like he had been building on the facebook app platform so he had been seeing that like his app was growing really quickly and his app wasn't a great business it was like you know those was like silly facebook apps but he's like facebook is not silly he basically took a bunch of that money and just plot he was like chris ak he aggressively started buying up facebook stock back then before it was public and and then he did and then he went to you know in in florida and he bought a bunch of real estate and i just thought wow this just really like conducting himself i i at that time i was just kind of like i thought of myself as an entrepreneur but i acted more like an employee like i wasn't playing the game to win i was playing with these like invisible handcuffs on me like i saw these companies that were awesome i didn't even go try to invest in them and like when i saw that this guy when he knew something was good he was like how do i take all the money i have and put it into this facebook thing i believe in this and simultaneously i'm gonna build my next business now you know right away and and so i just really admired i mean i thought that that was a great example to follow he's a hustle and and i like him a lot too let's go to the next question which is this what we'll answer this one quickly what do you not talk about or do we not have the chance to talk about because low priority or off topic that you wish you could talk about for me it would be i love talking about u i'm a big fitness guy so i love sports i love weight lifting and i like running and i wish we could talk more about like fitness stuff but i don't think it's on topic and i'm not an expert on expert on it yeah if i could do a podcast shooting in the shit about basketball the that'd be awesome but nobody cares what i think about the nba or or the really so that's one and the other one i think would just be like i do kinda bring this in sometimes but like it takes up a lot more of my life than i let show here on the pod which is like on the pod i'm just talking about a bunch of different business ideas ways to make money in reality i'm not just like doing that all day what i spend a lot more time thinking about all day is like but my mindset so what is my life operating philosophy and as i go about my day to be like the happiest and best person i can be and it's just kinda cheesy to talk about and like no one kinda gives a shit but like i give a shit a lot about it and i care a lot about it and i think a lot about it but i don't really talk a lot about i i do it i think about that too yeah but it's it is silly to talk about and it could be embarrassing particularly if you're still working through stuff right it's cool to talk about that i found when you're in a small group of people or you're in front of if you're in person with some people because you can get a sense for do they give a shit about this or not right and it's also like kinda of personal on a podcast you you might record that thing for an hour and you're like no idea if even if one person is gonna like wanna hear that or maybe the all turn it off what's you guys are awesome coming up with incredible ideas knowing how to execute them what would it take for one of you to pull out of twitch or i guess they meant in my case hubspot now and pursue it full force that's actually a great question and i have a i think is a good answer go for it which it which is first of all starting a company is really hard and i've like joked but i'm kinda serious i don't know if i'm ever gonna do it again maybe maybe not right or at least like who knows what i'm gonna do you know i've thought it'd be cool just to like retire and not work and we'll see if that's cool or not i don't know but i think that the answer far or the answer should be but it is not enough of i just think this is cool so like why are you doing this because it's fucking cool and i think that when i find something where it's gonna be like oh this is badass this is cool like there's not like for me there's often not like a mission where it's like let's save the world or let's it's like it's just kinda badass it's just awesome like right there's not there's no logic other than this is this is this is cool to me and when i i i found a few things that fit that but i'm still on a mission with hubspot and i wanna make it great and after that then i'll pursue the next one i get i don't like doing what i think sean you do this a little bit and a lot of people do i don't like starting lots of little stuff i prefer to dedicate my life to something and i'm very cautious about what i'm willing to do that with because you probably can only do that three to four times in your life and so there's a few things but i'm not i'm not finished with this chapter yet and that's why i haven't done it yeah that's a great answer i similarly i basically was like alright well what's this chapter of my life about and so when we got acquired i was like well i want them to feel like like glad that they did this acquisition you know what i like i want them to be like yeah that was worth it you know and and myself also was like well cool this is like a transition let me like try this new thing when we work at a big company never done that before let me have this like big c salary type of thing like never had that before i was kinda of just eating shit you know like doing my my own startup like sleeping on kind of an air mattress before and so so basically i was like if my twenties were about starting my own company and just trying to figure out how to be an entrepreneur what are of my thirties gonna be about and i've decided it was two things i said i wanna you know live a great life like with my family so you know popped out two kids in the last like eighteen months and so that that's actually like my project is being a dad and and having kids and spending time and just being there you know for that and not trying to be like oh i must because like you said now i know what it takes to start a company i know how all consuming it is so it's gotta choose wisely the second thing with choosing wisely is my thirties are about building a family and then it's building a project i don't wanna sell which is basically basically i totally agree how do i build my next thing same thing you said that this is something i wanna do i'm not doing it because it's the best business idea or it's a hot opportunity or whatever but what it you know so the thing that i just wanna keep doing that i don't want to get rid of i don't want to sell it i just wanna build it let it compound for thirty forty years and i love doing it and it's the thing i'm uniquely good at doing and i thought okay my maybe i'll dabble in some different things to figure out what that is and i feel like i found it which is like ironic i found it where i wasn't looking i started this podcast for a different reason but i what i realized was oh i really like this thing where i can be kind of like perpetually curious like i could just be curious about the world i can learn a bunch of shit and then i just share what i'm learning and i'm kind of like a teacher and through the podcast the email newsletter through experiments like all access pass or i'm gonna launch some courses in the future like my i launch school like basically i wanna do things like that something that lets me just be really really curious and learn a bunch of things and try a bunch of things and then share as i go because that's what i would do if i if i let's just say if work couldn't pay you money how would you spend your time that's how i would spend it might as well just do that as my work and so that's what i think i'll do next which won't look like a traditional startup or company and i agree with that i wanna do something that i'd never wanna sell so i'm in the same boat the question directed towards you but i'll give you my answer really quick which is sean how do you balance side hustle while performing at twitch my answer to that and i've said it before is i don't out i don't do anything on the side and frankly i have no idea how you do it our good friend ramon is able to do it really well i get some people can do it i personally can't do it and i don't even try and i'm not ashamed about that yeah yeah there's different ways to like kinda organize your time like you see this from elon musk or jack do running two multi billion dollar public companies at once as ceo right like of a crazy thing that kinda of seemed impossible before and i would say i do it two ways one is i throw more hours at it so like i don't take weekends off like i work seven days a week i don't work all day all seven days a week but i my weekend is just like my weekday there's they're the same construction so all of a sudden i got an extra sixteen hours on the weekend where i can do things same thing at night like i don't watch a bunch of like tv i stop watching like you know nba games stuff like that like i i basically it was like look i can cut that out and that's two hours a night that instead i can create content right or like when i do the podcast everybody else at the back when we started this everybody would go down to the cafeteria at twitch for lunch i would walk across the street the studio was your office was literally like fifty steps away from from twitch i would walk fifty steps away go to the hustle office we would record from twelve to one everybody else is eating lunch i'm recording a podcast cool i'll eat lunch on my desk like later it doesn't matter right so there's these little pockets of time you can unlock that's the first bit second it is hiring i bring on people so when i say i'm doing x it's really just me doing x it's like ben or zach or rom romaine or chris or i have a whole bunch of people that i say hey i'm doing this interesting project who wants to do it with me and they're like i find great people who wanna do interesting things together and i say cool what's in it for you do you want money you want learning do you want like rep you know want build your network what do you want out of this i'll make sure you get it and they let me like i said be in two places at once is why be doing this and they could be doing that what's your burn on all the like because whenever i hear you say you got all these people i'm like damn yeah that must be a lot monthly yes and but my burn is is expensive but the things now bring in money so it's it's okay it offsets it but like but the angel investing doesn't bring in money and that's angel investing i don't pay salaries it's only carry so it's splitting the upside so they have they they get they i took some of my my twenty percent carry and i took it down and let them have more carry so which you know for them is fine because they make money doing other things so they're like cool this will pay off in five years that's great and i get to like learn a bunch about investing i get to put together portfolios so if i wanna go get a job doing this or i wanna start my own fund i'll have a track record to point at and say no i i did these investments before i've i've been doing this for years so that's kinda like what's in it for them so i i do have a you know significant burnout i would say it's like two hundred to three hundred thousand dollars a year of like people cost to do these things my goal is for them to break even but if not like that's what money's is for money is to be invested in things that will grow and so i kind of like just look at it like an investment and it's worked out so far where where the side hustle more than pay for the money i put in now the last thing is basically an acknowledgment and i talked to i was pretty transparent with the people at twitch which was like look i operate not on a nine to five like strict schedule like cool i'm just gonna punch the clock for forty hours week no i'm here to do this mission you want this job done great i'm gonna get that job done here's the trade i i can make sure this job gets done you don't ask me how and when and where and why and how you know like all the like that in such a like conversational away but like it's an understood agreement like they know what i do i'm i'm very open about like hey i have a podcast i have a newsletter like the ceo of which twitch subscribe to the newsletter and like well dm me about it like sometimes right like i'm not hiding any of these things they know i do these things they know they take some time but they're okay with that trade because i deliver the goods in my projects and so my trainer told me this one day because i told him i said i'm feeling a little bit guilty like you know i wonder i really like these people i don't want them to feel like i'm short changing them he goes do you deliver the goods it's like well yeah like i'm i perform like they get the results they want so okay well you're that dude and i was like what do you mean he's like he's like they don't pay you to sit in your chair for certain hours they pay you to deliver the results and so just make sure you deliver the results and if you're delivering the results in less time that's because you're that dude maybe not everybody could do that but you could do that i was like oh man what a pep talk that was you know made me feel good about something that i was feeling you know uncertain about or uneasy about before and you're on pate opportunity leave now right yeah so that helps sue yeah exactly sales and and that's you know like big companies understand like look you if you have a kid my my first kid i only took ten days off which i really regret i should've have i should've have took the whole leave and so this time i decided i i'm gonna make sure i take some up and this time my family actually really needs me there whereas the first time i was like i know what the hell i'm gonna do here my wife kinda got it under control me go back to work and so this time i kinda realized that the idea of like oh this project is so important and like if i take this time off then you know blah well let me do it i'll take time off later and later never came and that was a big lesson for me like don't don't put important things off till later do them now who's the worst person this is such an interesting question k i bet you i know who that is who's the worst person you admire do you have one for this that's well like i it's a great question and it's you can get in trouble the answer this one i'm gonna tip to a little bit around it because it's just weird but i actually love learning about dictators i like i read a ton about dictators there's actually a podcast called dictators so like i like learning about anita mu i read a lot about hitler i read a blood about fide fidelity castro who else so i think i got in trouble with this before because i remember i was in school and i took a history class and the question i asked the teacher was look this sounds so messed up what was going on back then this sounds totally screwed up like how did this guy come to power and he explained like well here first shift to understand the state of germany at the time blah blah he goes the other thing was that like honestly he i forgot who's hilary second in commanders but he's like kind of like a famous guy for like his almost like his persuasion prowess like his his marketing prowess yeah joseph stuff give yes yeah he's like the head propaganda he exactly made movies but exactly sure i forget it the same he's kind famous guys he's like his number two guys that head of propaganda exactly and they did very simple things like everybody else was putting out like i forgot like they're flyers when they were running for whatever president whatever they're equivalent a president was was like all in color he did everything in black and white to stand out or if everyone's black and white he did color like he just did a whole bunch of things i found it really interesting like oh like a go global doctor go yeah yeah yeah yeah yeah so so they had movies made and they used entertainment to kind of like get their message across you get the story across they had like a whole bunch of like dis they dis distilled down their philosophy into these really catchy nuggets and so there's all these things that i thought wow that's like if you just abstract the good and evil away the skill of accomplishing a very hard thing which is like getting millions of people to follow you there's a lot to be learned from that and i kinda was like oh that's really cool and people were like dude you said hitler's cool like you're you're on yeah that's you know and that's that's the point i'm getting at which is like it's so fascinating that someone can convince in in my opinion like a lot of dictators i'm like man if they like just like move that early on like clicked it a few notches to the left and then that trajectory would like put them in a totally different atmosphere i'm like man it like it but it is fascinating how someone can come from nothing and just create something whether it's an idea of business a piece of art whatever like i love that like idea of manifesting and even though it's horrible and the worst thing on earth and i wish they'd it never existed i always have been fat fascinated aid by like a guy like c rivera or someone who like was this like or what's his name ben mu who i just read about like this wasn't like supposed a poor kid and somehow he convinced all these people these to do all this horrible horrible stuff and that like to me is fascinating how he just bent the world around him mike and like that's just crazy that hey people buy into that stuff and it's crazy that someone that he had the courage to do that which sounds like i'm glam these people i'm not at all but hopefully you guys understand the nuance here and and and why it's kind of intriguing yeah took two things one when i met i've talked a little bit about my friend vis michelle the guy who's kinda like a young guy who i'm like guy's definitely gonna be a billionaire and he's also kind of like totally hell bent on becoming a billionaire and he lets every part of his other life got like what we were talking about earlier where i was like well on the podcast i talked a lot about business and money but like in my real life i'm doing i'm really actually more passionate about these other things i i spend more time on he's the opposite whatever he talks about here he's ten times more obsessed with it outside of this and i love him for that and i remember when i met him he was he he was like send me this documentary about like just like warlord in africa who just like just like the get like the absolute like gang gangster shit this guy did he's like i love this movie i love this guy i was like was kinda like heinous crimes you know he's like no it's crazy man told me the story about this guy who became the emperor of china and he started off like as a like an orphan like servant and then ended up by the end of his lifetime as the emperor of china i forgot his name but like one of the ancient of china was like started off as an orphan boy with not a dollar to his name and then like rule i mean it sounds like a angus khan or something yeah and he was like like not just like i got there like it's not just a hero story like he also like you know like sla his enemies and like enslaved people or i don't know what he did but like it wasn't all you know just like underdog you know it wasn't just david and gl and he told me that story and i was like euro man but you know i actually would love to invest in you because that's the kind of like man you want being a founder of these companies like somebody who is wired a little bit differently and as i remember hearing that but anyways the phrase you say that's like every great man is also a bad man yeah that's kinda true everybody i like my favorite comedian is louis ck k who i believe is canceled for you know like doing something gross front of a bunch of women or whatever you know like and i don't think that's cool but i love ck k and i still love c k and like i think he's awesome as a comedian i didn't say he's an awesome character you know that awesome human being and i wanna be him no i think he's an amazing comedian and i love his comedy conor mcgregor you i had a poster behind me of him you know painting that i had made of him behind me for half these podcast podcasts he's been accused of sexual assault he's been you know he people say he's on drugs and he's kind of a asshole and like other things too he's an amazing fighter and i love his driver of how he went from like a plumber on welfare to the wealthiest fighter of all time and he said the whole time from the very beginning that's what it's gonna be he called it and there's videos of him he's alone in his bedroom not even a professional yet and he says i'm gonna be the greatest and here's what i'm gonna i'm gonna do he hey he did it all i admire that but i also think he's does a bunch of sc shit and like i'm okay with that you know so there's a bunch of people that i like that i was driving me and sarah one time we're driving by chick f a and we're were like i wanna get that if you want that and she was like i want that so bad and we're and she was like but do we wanna support them this is right when they like did some stuff anti yeah and we were like well my case buds don't really know if you're homophobic so right i think we'd be it it's okay i think we could like the chicken but also or it it was something maybe we were at some place and they had the chicken there and i was like i don't think my taste buds could tell if you're homophobic or not so we could probably eat it alright let's answer a video question lot lately i'm thinking about trying to hire my friends as operators of sorts and i'm just worried about like damaging that relationship like i think it's an awesome idea of being able to choose i work with i'm just concerned that all that friendship could go away when there's something as important as like business and money involved i have a pretty strong opinion on that which is no i think you actually shouldn't in most cases don't do it in some cases it makes sense but in most cases i actually think it's a bad idea and i also have myself failed at doing this a little bit but i actually don't think you should be friends with your coworker or your friends with your employees if you're a manager you shouldn't be friends with your employees if you're a a business owner or a ceo i actually don't think i think you should be friendly but i think you should be really careful about being friends with your employees and so my opinion is no i also think that like you probably disagree sean or maybe you do but like even if they're if you're worth your coworkers workers and anytime in the evening and alcohol shows up i think you should leave i don't even think you should be in the same room so i'm pretty strict about that although i am friends with a lot of my coworkers so i don't exactly follow all this but it i think that i'll might regret some of that we're opposites on this so you know what's it's funny i always try to be friends with my employees and i feel like they don't wanna be friends with me so i'm like yeah i'm like hey i'm trying to be friends with them and then i'm like oh that's weird you guys all got together this saturday and like oh yeah i just at home could've could come yeah well what funny is like when you like start a business and you work a lot like you don't really have many friends like i have conference friends with you and jack and her ramon and like four i've got like four friends but my coworkers are so like i'm like will you guys be my friends i'm with you on time and i don't get invited to anything either yeah so i i realized pretty quickly they don't want me around and i was like but it's weird i'm such a good guy and so anyways that that part didn't work not because i i didn't intentionally try not to be friends with them they just didn't be friends with me back that's okay the main thing for for me on the hiring side is i would say hire your competent friends so my very first business i started i started with two of my best buddies from college and we were just like yeah we're gonna do this we you know well and there's no ceo there's no hierarchy here well just make decisions together we're all split the equity perfectly equally didn't really like put you a thought into it because we were just like twenty one year old kids didn't really know much about anything and like fast forward a year later we had to have like very uncomfortable conversation with one of them guys which was like hey dude like i feel like you're not pulling your weight and he was trying but like we were just like you're kind of just doing this parts and like we're we feel like we're doing these other eight parts and in retrospect i don't even know if that was really true but it definitely was an uncomfortable conversation and i could see the downside of it but i what i would say is like the the saving grace for me has always been i only have hired my competent friends and competent friends do two things one is they perform so you don't have this you're not just hiring a buddy because of your buddy you're hiring this person because they're good but you only know them because your buddy the second thing is they are reasonable and they will under they will understand if you're really clear up upfront about like look here's the dynamic like we're buddies but i sometimes i'm gonna have to tell you if i feel like job's not getting done and i actually i want you to tell me to if you think that's true like are we okay if it's gonna be kind of uncomfortable like we're not just gonna be able to just shoot the shit like we gotta also have these two modes that we can operate in and i wanna make sure like you're on board with that so i'm i think with a with a little bit of good communication upfront you can get the big benefit which is it's way more fun to do stuff with friends like companies are hard to take a long time it's like a really long road trip and you wanna be in the car with people you really like and so whether those were new people who you just happen to enjoy great or they're people you already enjoyed who you invite into the car because they're buddy and you wanna do this company with them i think when it works when you do it with your friends it's the best and when it doesn't work it's even worse than if they were they were not your so you gotta take the good with the bad but we had a podcast with this guy on the feed called mike brown he you introduced me to i met him at your office yeah he's shit he he had a successful business and he brought both of his brothers on board and i was like why did you do that let most people say you know don't do business family gets messy he's like these are my brothers i love these guys i wanna see them every day i wanna hang out with him i wanna win together i want us all to win he's like i if he's like i feel blessed that i got to set this up where i get to do business with my best friends and i was like but when you say like that like what the hell am i thinking about that's obvious said that sounds great and so i think there are downside but i'm of the mindset of if you pick competent people you won't regret it alright we'll do a a couple more bass questions someone asks who could squat out more weight i think i think me definitely you i have i have oz sc in my knee keys if you if you have it you know if you don't have it you don't know but because of that i don't squad i can't spot i never squat my whole life because of that issue okay this is a deep one it's cool well we'll answer it what your biggest insecurities both one are the biggest insecurities both of you struggle with i'll say i'll go first sometimes i'm i i get incredibly insecure that anything i make won't be good enough because i moved too fast and i just do surface level shit and i don't treat it like a craft like a craftsman enough and i don't like think things through i get pretty self cautious when i meet really smart people who i meet a ton of them through this job i'm like oh my god this person's like i huge just like they so much smarter than me i just cannot keep up like because so i i i'm insecure about that i'm insecure that i like i didn't go to stanford or like a fancy school and when i meet people in the in crowd like when we meet guys like andrew chen who who who works in injuries h i'm like dude not like i kinda wanna be in the in crowd but like i don't wanna work that hard to do it and i just don't care that much but i wish i did but i feel a little insecure about that and i feel get insecure because i'm pretty loud and that sometimes makes people not take me as seriously as i think this should so those are mine those are really good ones and i think very relatable promptly for most people mine i would say i i don't know if there's insecurity as much as like because when people say insecurity it's usually like what's something you worry about but it's not really true but you kind of worry too much about it i think mine like is true just more like here's your weakness here is your you know your your weakness so you're you're flaw i i would say like and something i i i kinda worry about which is i don't really filter myself and i so i just talk a lot and i don't really think about it before i do it i don't really think i don't even filter myself with actions like like i said i with the rolling was like oh that's cool let's do it so can we do it today let's just do it now i don't wanna think things through and so i would say that fear i have and the insecure to have is around actually like hurting people's feelings like sometimes i could say stuff that's in inc inconsistent or or hurtful in some way or like you know too opinionated and note they didn't nobody asked for your fucking opinion type of thing so i i'm kinda conscious of that like i i would say pretty self self conscious about that that that's the word not insecure i'm self conscious that while i do that and i don't really like that part of me that like i will say things and do things that i don't really think about how that how other how how others will feel about it and and also like when i meet people like our friend ramon who's so considerate i just feel so inc inconsistent in comparison i i wanna be that way but man i'm like the opposite and like you know i'm like so i'm like a knuckle drag i'm just like yeah a mean t so i feel really bad about that and then i would say like the other minor in security is like am i just wasting my talents like so when i meet people who were doing really amazing things like scott harrison you know he's been on a fifteen year mission to bring clean drinking water to the world i went with him to africa and we went to a town where they had installed one of the water wells and literally the town was like it was like a parade that scott was here literally thought this guy was jesus and he kinda like looked like jesus in the moment i thought he was jesus in the moment and like he's totally humble he hated that they were celebrating him he was there like not for that reason but that's the reality of the impact of his work and he literally changes like the lives of entire like towns essentially in africa and and so then when i see that i'm like what what am i wasting of do i need to do this silly e commerce thing do i to do this newsletter who gives a shit you know and so sometimes i feel really small about the way i decided to use my time and my talents completely agree with that compared to other people last question when are you guys gonna do since covid it's pretty much in the past when is the next meetup gonna happen i'm actually doing a so i'm driving to saint louis to spend a week with my family there and i'm stopping in oklahoma city because that was just like the middle ground and i tweeted out so i've got like thirty or forty or fifty people i forget how many people are rs pete for a breakfast in oklahoma city and if you're down sean although you just had a baby so imagine we're gonna have to wait a little while i would totally be down of doing like a two week tour or something where we go from place to place to place i don't know if we could drive i don't know what you'd wanna do but i'm totally down like a two week thing yes totally agree i think like if we just said alright this fall we're gonna go on tour we're gonna go to these seven cities seven cities and seven days or seven cities and ten days or something like that and we just like set up the events i would love to do that i think that would be just well we just we just hired a community manager her name's april and she set this event up for me i said hey i'm gonna show up in oklahoma city can you get like can you book me a hotel and set up an event right and i'll tweet it out and we'll we can have her do that and help help out with that you do something really great that i think you should tell people which is when you you hosted events but you make the themes great so like you used to do this thing called pizza and forties so can you give me i i don't even know what other ones you've done but like tell the people of some of the different events you've done because i think it's really smart when you set those events up people wanna come and they they behave differently because of the theme of how you set up because i've been a lot of silicon valley networking events are boring a shit you don't wanna go and when people go they're all like surface level level like they you know it's not a fun place to be they don't let their guard down your events are very different so can you what are some of the different themes you've come up with and like do you have a theory on why that works no i don't have a theory i just think it's fun i do it for the what i said earlier in the episode i it just because it's cool that's the only reason why so i do the anti nba that's a book club where we get an expert to come in and discuss the books topic i've done this sounds douche you to say but like i don't even drink so is why it's funny but we have this thing called pizza forties so the speaker gets a forty ounce beer because a forty ounce spear takes like an hour to drink and as and so we only would have pizza because we are poor and that's all we could afford and we give the speaker a forty ounce beer they've gotta drink the beer and when the beer is done the talk done and the answers get a little bit while they're as they get deeper into the beer we did two x which was focused on women telling their story it stands for two x chromosomes we had like did you go to the one that we had in the marina no what's that we used to do two x at this thing called palace fine arts and we had like literally two thousand women there in san francisco it probably was like the largest contingency of like tech women probably in the world or in the country it was kind of interesting so we did that what else did we do hustle con con con which is con con is the startup up that's the content conference i thought con con was a funny name what else anything else have you i feel like you've done some breakfast thing before have you done a breakfast thing grind yeah we did rise grind which was we would talk about different stuff in the morning over and like a grind like coffee like coffee but also like work hard crying you're good at this you're good at coming up with kind of a catchy name and a catchy theme for people to get behind and the vibe is very different so i think that's if somebody's doing it like that doesn't take any extra money it just takes like a little creativity and know you've major thing better and cooler more fun for you to do more fun for people to come to more fun for speakers to attend because it's different than the average thing so long story is short maybe late summer if you're down yeah i'm definitely now alright great that's it we'll do it yeah i feel like i could rule the word i know i could be what i want to like travel never looking back