25 Years Of Founder WISDOM In 55 Minutes (ft. Jason Fried)

my job as a founder it's to inject risk into the business you can get away with certain things that other people simply camp because you own the dang i feel like i could rule world i know i could be what i want to like alright today's episode we're gonna talk about things that interests us one thing that i tweeted out the other day i wasn't surprised by this result but it still made me sad i tweeted out i said if you could guarantee a seven and a half percent real return for the rest of your life every year guaranteed but you can't invest in any individual stocks forever however you can start your own business and i think i even said you can but you can only invest ten thousand dollars into that business or you can invest actively you can't really buy the index but you can invest actively and do whatever you want some days maybe or some years maybe you'll get plus fifty percent some years you're gonna get minus fifty percent which would you choose option a or b forty percent of my three hundred thousand followers selected option b and you replied and you said option a all day easy what why did you select that well to get turned about seven point five percent like with no effort and you're guaranteed it's a no brainer it's an absolutely no brainer for me i mean now i've got a business i a lot of risk in my own business so that might be part of it as well like i don't i have all the risk there so let me ask you this were you intending this to be like someone who's twenty one years old strat school never invested before has nothing else going on or is it just like at any point in your life i think at any point in your life that's still the right decision i still turn that switch on in a second yeah that's a ridiculous return in in a good way and a consistent return i mean the the way that would compound over time would be fantastic and there's nothing boring about that that's an incredible i mean it's boring actually but also an incredible thing so yeah what would you think that the the the survey was gonna produce did you were you surprised by the ratio or i'm surprised that the average joe i mean and my followers are probably above the average show in terms of income maybe iq maybe not i don't know but for their they're typically a higher books for sure they're they're up there they're very good like it's a very high i like i imagine it's a high educated coastal crowd and and so anyway i i i would have thought that they would have seen the fallacy that they probably can't beat all the others particularly the other people who have a much better advantage and so the idea that although everyone else fails at getting this return i in my little office in part time with just me can somehow beat all the others and i and i thought that that was shocking to me that that they thought that they're were exceptional at that that's what i was surprised at yeah well that's pretty common i think everyone thinks they're exceptional in some way i mean the thing people don't take into consideration is is is is risk so like they they might go well if i just buy nvidia or apple or whatever shopify i mean and the thing is in the short term you almost certainly can over the two or three years you get lucky pick one pick a winner but the rest of your life that's the question so here's what i've done lately i've been spending time in new york because i've got family here and i called the email then did call outreach and i randomly met a bunch of people who work at hedge funds and i'm like hey like i'm not like a competitor you don't ever have to worry about me i'm just like a a passionate interesting interested person can i just like see your office and just like can i just sit at your computer and you just show me your software and like i just wanna see like what you do all day and you go to some of these offices and you know i would have thought like they were like waffle wall street where it's like buzzing and like the phones are ringing it's really just a bunch it's pretty quiet and it's usually just like a bunch of nerds like looking at a computer screen but they got like four screens and they've got like incredibly complicated software and the average show is getting paid hundreds of thousands sometimes tens of millions of dollars to be good at this one thing and then i think about like how is like bobby lee in whatever missouri where i'm from on his robinhood app possibly gonna have like an edge on all these resources and these people with all these resources they're still not that good you know i talked to a guy who worked at bridge water recently and i was like bridge water i run a ray dal or you guys like the best he's like sometimes we're the best but the last fifteen years we've sucked we've under performed the market and i'm like that's insane that fifteen hundred employees tens of billions or hundreds of billions under our assets you're all paid like the best there is you still can't beat it and so that kinda like that's kind of where i'm coming from yeah it's also like vegas you go to vegas and you know you've you're on a hot streak for for thirty minutes and you know the longer you play the less you're gonna win you're gonna lose like but you're you're gonna lose the house is going to win over the long term so people i think have this idea of short term performance in the market feeling like i can i can do this forever just like in vegas you can't do that forever and you will begin to lose and the same thing as true in the market so yeah lock it in what's this thing about loosening the grip on the stick oh yeah so i got i got a drum set recently i i used to kinda wanna play drums i kinda did for a little bit i stopped for many years that i kinda just picked it up recently my office is a bit of a mess so i gotta find better place for it but right now it's in the corner and as i've been playing i i i i learned this very quick lesson and actually it's true when i try to learn how to play guitar i say try again because i'm i'm not very good at these things but i i enjoy them is when you're new at something you tend to hold things too tightly like i i hold the drumstick too tightly i hold the neck of the guitar too tightly anyone who's played any instrument will understand kinda where i'm getting what i'm coming from here i used to play drums i know you're talking okay so you you hold this stick really really hard and then you fatigue faster you don't have as much articulation on the stick you can't get certain ghost notes and tones out of things because you're always hitting too hard and too firmly and you just there's no finesse and it kinda dawned on me recently that this is very very true for most things in life i think in especially business i kind of some ways i feel silly always bringing this back to business anyway i realized that like by simply loosening my grip a bit by lightening up you end up having better control you end up playing better you end up working better you can do it longer and you allow other things to happen that weren't possible when you're gripping so tightly i think this is true for business i think when you're starting a business you have a really tight grip on things typically and it's best at some point to loosen up a little bit and let the rest the organization expand into itself versus you trying to control every last thing and i run into a lot of entrepreneurs who i think have not learned how to let go of the stick i think that that's also a young man's thing to do right like you learned this with age what are you saying what do you what do you what are you trying to say well what i'm saying is you you you you have a couple decades of experience and and like and so do and i think that as i'm getting older which i'm not old but neither you i'm learning it is okay to loosen it up that's what they say a lot about men they say oh well she used to be intense but he's mellow out he's mel it out and that's usually what they're referring to yes that's a good point yeah the mellow out it's nice though in in a different realm of something to to find a metaphor and in in my head now i am kind of thinking about this like loosen like loosen up your grip a little bit in what parts of life well i'd say business i would say also like with my kids a little bit i i i would say there's a way where i i kinda wanted wanted them to do certain things a certain way and and it's just it it creates this conflict like they're their own people on my own person and you know i wanna encourage them to do certain things in a certain way but i gotta loosen up a little bit around that and let them find their own way and that that's something i kinda learned pretty early in parenting so there's a lot there's a lot of things but i just in general just feel better when i'm not gripping things so so tightly and what i look out there you know on on twitter or or anywhere linkedin or whatever and i'm i'm looking at these like business stories there's just i'm i'm reading a lot of grip i'm reading a lot of tension that that you know people are trying to up over optimize and paying attention to every last little thing in a way where i feel like just loosen up a little bit like pay attention a few things that matter and let let it let things just be a little bit more the best example that i've experienced this in my real life is arguing with people and so before it was like every word that i like when i learned to talk it was like it was fight was the first was the first thing that came out you know like my early words where i wanted to fight and so if i met someone with a different political perspective it was you're wrong for these reasons that you're really stupid for that when i lived in san francisco i i was it was was significantly more combative than i am nowadays as i yeah i've been lucky that i was raised in missouri and that i lived in san francisco lived in new york lived in texas and that has shaped me a bit politically but also that it it it bleeds other points of life which is like instead of someone saying something when someone says something that i disagree with it's more so instead of fighting it's well why do you feel that way that that's that's a really interesting perspective tell me more about why you feel that way and i think i i don't know if this is just a clickbait thing but keanu reeves had this quote where he was like i used to argue with people now i never argue you could say one plus one equals five and i'll say well i hope you have a really good day and and that's a little bit about how how it's been where i just wanna argue a bit less and i'll i'll still catch myself arguing but dale carnegie in this a how to win influence to how to friends win friends and influence people he's got many famous lines but one of the famous teachings is basically just don't argue with people because you know party typically walks away happy or satisfied and so loosening the grit for me is arguing less where it's i'm not even gonna judge you and i'm just gonna i can recognize that you think this way and i think this way and it's cool it's a great example actually i hadn't thought about that but that that's another great example just like holding on not even holding on too tightly to a perspective because you you can have a perspective that you really believe in but it's it's it's you know it it's like don't cl or you're not even able to listen you now i think the the point about like being too grippy is is your you're you're it's like you're a spring under tension and if someone says something to you that you disagree with like you're gonna boom expand and like explode right which is kind of what an argument can be versus just already you're taking some of the attention out of that spring and just like bouncing within it and listening versus exploding out of it i think that's a big difference have you ever read there's there's this term i'll have to figure out what the term is but there's this term where astronauts go to space and they see the earth from far away and many of them have reported to have a life changing perspective where they think to themselves the fact that we're fighting over religion is ridiculous the fact that we're fighting over borders is ridiculous now let's zoom down to the smaller things the fact that we're fighting over someone saying something rude to us is absolutely crazy because we're all just a bunch of monkeys on this like floating thing and it's monkeys with cars and like we are yeah and we see like this this abyss and then we're just a silly blue thing in the middle of it and and and it's like a lot of astronauts say it changes their perspective and it mellow them out and i think that when i read about that years ago it kinda helped me calm down a little bit more to where you think not the the stuff that i thought mattered doesn't matter for example i remember when covid happened and i was like we're never going to a concerts ever again and then three years later i'm like fuck that that i forgot all about that do you what i mean totally have you have you to that point about astronauts have you read that great passage from carl saga in the the pale blue dot what he say no i mean it's one of the most beautiful i'm not gonna say it because i want get to read it i want you to have the experience sure it's a paragraph it is one of the most beautiful passages i've ever right but it's it's exactly kinda what you were talking about with the astronauts it's like looking back at the earth it's all about all the things that have ever happened i'm gonna really generalize here because i want you to read the words but all the things that have ever happened every leader every religion every point of view every argument every whatever right beautifully in beautiful prose happened on this speck of dust basically i think it calls it like a moat of dust it's such a beautiful passage and it it brings to tears to my eyes and i tried to read it a few times a year because it's so right it's so spot on right it's exactly what you're were talking about in the most beautiful poetic way which is all the stuff that we're worried about all these things like very few of those things matter of course they matter in your day to day life so like they're real for you but they really don't matter that much it's just a good reminder that you know all the things we're just so fired up about cares well it's a it it it's a paradox of like caring by not caring why do you not like comparing this stuff to business and i'll afterwards i'll tell you my reason why i think is good yes so this is an undeveloped thought of mine that's been sort of on my mind i don't know if it's a good idea or not so just run with me i'm gonna i'm gonna kinda this is undeveloped it seems like every great lesson is then applied to business by someone so for example a navy seal learns all the stuff in the military and they come and they like then consult for companies about how to like run teams or some great coach coach is a great team and then they come and they bring it to the business world it's always like bringing it to the business world and i'm like what does the business world deserve the best lessons from things that are completely unrelated in them many ways to business but why does always come to the business world and the main reason is why in my opinion is because the business world pays for that advice it's not that it deserves the advice it's not even that it's advice that's applicable but that it pays for the advice and the way i've been thinking about it is not as this this this this shining beacon on a hill that business deserves all the greatest things but actually as the drain that all these ideas drain down through business because business sort of just is willing to pay for it and and listen to it and sort of have this this this it's sort of insecure way so like it's it wants to listen to the navy seals it once to listen to the great double or and and nc double coach it wants to listen because it it's insecure in its own way and also there's this there's a sense of like these other places and people they know better than us so we're gonna we're gonna just you know bow down for their advice and i don't again this is a little bit uninformed but it it's something that just bugs me a little i don't know is does that make any sense or yeah is it just a weird idea no it makes sense but my argument would be instead of the image that you've had you just painted is you've painted a upside down triangle with all of this beautiful stuff draining down just bad thing thank you i would turn that turn that upside down say it all is going up to this amazing thing and here's why because i think that whether you like capitalism or don't like capitalism you cannot deny that's here to stay at worst it's here to stay in the lifetime of everyone who's alive maybe america will change maybe maybe the rest of the world the majority of the world will change but i i i wouldn't bet on that happening anytime soon therefore i think that capitalism and thus business building is the most practical way to manifest a dream or a reality and oftentimes you could say well what about art and i would agree with that but at the other of day you're still making stuff that people want and you're still selling tickets you're still trying to make some type of money off of your art so you can continue doing it or you're just gonna have a rich person who funds you so you are are able to do it and so my opinion business is the most practical way to actually kick a dent in the world or to manifest a vision and so i think a business as a very path like i'm very passionate about it being a little bit of a spiritual journey of like turning dreams into reality that's an optimistic point of view which which i i do understand here's my question if this thing called business is absorbing all of these lessons from all of these other realms right and they're all like either filtering down or filtering up but they're filtering two and maybe i'm wrong about this but why aren't the navy seals asking ceos for advice why sometimes they are if you look like i don't maybe they are like jack welch book six sigma like a lot of different types of organizations out set of business like view that book i i don't really like that book but they view it as like the rules of the game yeah okay yeah i might be uninformed in in a sense of like what who the military is listening to and who you know worse teams are but there's something that's like you would imagine this this this entity this business thing that has absorbed everything would then be the definitive source of this wisdom but i wonder is it a one way street or is it a two way street and seems figure one you're more right than you are wrong that's for sure it's definitely more one way yeah no i just wanted to give i just wanted to give one example but i was yeah frankly it's a nit pick example totally i i don't i don't know i again i don't know if this is a good idea or not it's just it's been sort of floating in my head for a bit so i it's fun to air these things out what was more fun early days early late days of the company man that's a really good question they're very fun in very different ways so i again it's a bit of a cop but it's it's true but their fun in different ways what's exciting about the early days is there's a certain energy that you can never capture again which is the the there's so much more unknown like you're you're you're you're starting from zero and you're building something and you don't know where it's gonna be in words gonna go and what's possible and what isn't and how long it's gonna last and all those things now you don't know long it's ever gonna last in a sense but there's this there's this hope there's this possibility there's this birth and you know it's like boom we're out in the world and here we are and this is an incredible thing and that's super fun and then you get a lot of a new attention and you're kind of burst on the scene and that's exciting really exciting i think what's what's hard actually is the middle we've gotten to a place now being having done this for twenty five years it's become really fun again in a different way but i would say like fifteen years in is a different story because that at that point it's like we've been doing this for a while i don't know how much longer it's going to last like you're kind of in this sort of maintenance thing were you big enough at fifteen years where you're like like payroll is not an issue like were you out of like any type of outside pressure where it was like things are fine i so it's like i feel weird that i i'm complaining but this feels weird yeah and i'm i'm not really complaining about it but yeah yeah it's more like you know scott sc scott be wrote a book called the messy middle that's great have not read the book actually but i understand the idea of it and it's kinda what i'm trying to get at which is like the middle of it is it's like what do we wanna be now and and where do we wanna go now and are we were gonna be a big company are we gonna stay a small company there's all these opportunities that are surrounding us now and swirling around us versus when you're starting you're just like you're just going you're just moving and then you just play place where you're like kind of evaluating and now we're in this place where we're just sort of mellow in a sense to your point although we're actually getting very ambitious again because we have the sense of like we've been doing this so long now that like if we took some crazy bets or made play some crazy bets and it just totally all fell apart like i don't want that to happen but i'd be okay with that too like we're at the place where it's like we've done plenty and we've had an incredible run and if it all ended with a bang because we tried some crazy stuff that didn't work like i'd be okay with that too so i feel like i at that place now what i wouldn't have been at fifteen years if that makes any sense so your sense i mean you start a bunch of stuff my sense is that so none of my things have had been as big as yours but they've been big enough where we've had dozens or you know fifty sixty employees and it it we got outside of the like existential crisis moment where it's like things are working my and and everyone talks about focus focus is a very common thing and it's something i i firmly believe in but someone who likes to make things for my skill set a company outside like maybe let's say three million in revenue or maybe maybe five million in revenue i'm noticed consistently a five million in revenue and like fifteen employees something like that i'm like i don't know what to do it with my hands like i'm just sitting here like what what how do what do i do i feel useless and i feel like sometimes a general behind the scenes just pointing and i've noticed something that i i i really dislike but i think it's normal is a company ebb and flows and i've noticed that this ebb and flow carries over to the rest of my life where i just had a child and i'm like i'm in this quiet time for a moment where i have to be present whereas there's other times where you're dating or something like that and you're like i'm in i'm i'm in more mode a little bit where it's like there's it's action constantly or like i'm on top of my game and i gotta be top my game same with business where it's like we're launching this new thing we're we're out fighting with the troops we're in the trenches and then there's other times sometimes this i think can last for years maybe where it's just like it's we're just doing the same thing over and over and over again and that period can be a little depressing even though everything is going well it's a very sad period because you lack action it's basically like what they say with a lot of great investors i think man said this on our papaya on our last podcast he was like if you can watch paint dry you're gonna be a good investor the problem with that for a lot of in a lot of entrepreneurs or a lot of like go get is that's a really sad place to be in even though everything is going well it's really uncomfortable to be in that feeling and so have have you guys had a lot of have you had a lot where you're like man i just gotta kinda unfortunately have to do nothing for maybe years yeah i can totally identify with that and i think i think what you're getting at is with entrepreneurs is that what you're describing is in the early days you are very important as a founder yeah then there's a point where you build an organization and then the organization is able to in some ways in a good way run without you to some degree and at that point you kinda feel a little bit less valuable yeah to your own thing that you made it's a good thing but for you it's a good thing because it means there's some stability and you're not the bottleneck and you're not the only person that matters here anymore obviously but but for you personally it feels a little bit like you've become detached from this thing that you made and you you're now further away typically from like the the the creation phase and now you're more in the maintenance phase of something and and you're dealing with internal politics and personalities and hiring and you've got some great people who just left and now you're gonna find new people and the culture is changing and like that's a pretty tumultuous turbulent time for a founder and i've gone through that many times and it it it comes comes in it goes what i found is that what i kinda discovered actually recently is that my job as the founder i'm still founders i still started this company i'm still in it twenty five years my job as a founder what i've realized is is it's to inject risk into the business most people everyone pretty much at your company job is to manage risk to some degree to keep their job to not push too hard or too far ultimately you can get away with certain things that other people simply can't because you own the damn place you are the original person so what i've found a lot more joy and and and excitement in is is revisiting this idea of injecting risk and for us that means by the way i i don't think you could change that i think like for a long time i was like why aren't these people taking risk i gotta force them and i'm there you go it's impossible that's impossible to change even if you are hire a great great ceo to replace you with like they're they just don't have that there they might be in an incredible ceo great executive executing things trains on time incredible but there's that thing that's present in a founder simply because they were there from the beginning that they they have an extra ounce of it's not even that they're they're not better they're they just have an extra ounce of latitude that allows them to take risks that nobody's is going say no to maybe if you have a aboard maybe someone's gonna say no but they'll still give you more latitude than a hired hand basically in a sense so my my sense is the way i found to return to this sort of flow versus the the app is is like is to inject more risk which for us means we're gonna build a lot more products like this year we're gonna do four products we're gonna we're gonna begin we've we're about to start working on two products simultaneously which we've never done before we've never built two things at the same time and like this there's a lot of stuff going on we got different models we got once we got saas we got all these things we're gonna do multiple versions of multiple things in different different business models and we're we're doing we're really off balance in a really healthy way at the moment because like we're doing a bunch of new stuff and that gets me excited now it makes some people internally nervous understandably so it's like well this is different now where we're kinda off balance a little bit and we're trying new things but that's how i have to run the business otherwise i will become bored and at that point it won't serve me or the business well if i'm in charge and board that's that's not a good that's not a good for my professional life for for my main company that's like the main nine to five thing for hampton i've not i do inject but i have a ceo and so i tried to i have to like respect i gotta respect that relationship and so yes my nights and weekends i i created a new website for fun i created this website called sam list it's sam list dot c nice and the reason i did it was i tweeted out like who's got an accountant that they love because i just needed an account for something i got like three hundred replies and i was like wait something's interesting here because this tweet got so many bookmarks like a lot of people bookmark and someone was like oh i'm saving this for later to find an the accountant so i was like this is interesting so i spent a few months calling every accountant on the list finding out how much they charged what service is they provide what services they don't provide who the ideal client is who isn't the ideal client whatever and then i created a website called sam list where i reviewed or i like put all the information from all of my research for all these accounts created this website i think i got eight thousand people to come in the first week and then i started figuring out how to monetize it and so this month that the first month that's been live it's may twenty second when we're filming this i think it's done twenty thousand this month and the twenty thousand dollars that i've made from that is more dopamine than let's say a million dollars a month or two million dollars a month that i've gotten from other things it's a total rush and i love it why is it why do you think that why do you think that's so exciting for you it's a total rush because what started it's so fun it's so fun for things that start as silly jokes like like just stupid like the calculator like the the logo that we have is a calculator that has three numbers in a queue and it looks like clip it looks like clip from microsoft like waving at it you it looks like mickey mouse and i just use chat gb i said make a logo that looks like clip but it's a calculator and it's so fun to take silly joke stuff and turn it into real things that actually solve problems and i find that to be almost like part trolling part like shit eating g like scheming like i love that like isn't it would it be hilarious if we made this a thing and then actually seeing it become a thing i find to be so exciting i also think that when you're when you have a silly idea even if it's like a serious idea and you start seeing customers truly like it that's a very in feeling it's the best and we we had this internal say we don't say it that much we've we i i've said it before and we kinda try to feel it which is that cool wears off but useful never does and what you've made is something that's useful and that is one of the most beautiful things i think you can do for humanity to make something useful and and to have fun within the screw and not like take it so seriously this is going back to the thing your your grip is loose on this you know you're having fun with it yes gp to make a logo and you're goof around and the name is just your name but it's like it's just have some fun and and it's a reminder that that's what this should always feel like as much as possible it is totally valuable to do hard things absolutely but not everything should be hard there should be plenty of easy things in your life too things that flow things that you have fun doing things that don't feel hard you don't need to pile up and collect only hard things and so while some of your business ideas might be harder to pull off for other reasons this one is so light hearted and easy it's healthy it's good for you and you red discover like why you do this sort of stuff and it's also fun i think there's something probably i'm guessing there's something probably in this that like you're like i did this by myself yeah that's like the feeling of accomplishment and go i you i can still could still do something by myself like really by myself and that's useful is is is very rewarding and and hard to come by sometimes when we all think we need to have partners and c founders and teams and stuff to pull things off do you and your partner get along like beautifully we get along really well we're not like we're we're friends but we don't see each other very often we live in the same town and we don't see each other i see them once every i don't know couple months we're very good partners and we're friendly but we just don't we don't hang out like our families don't hang out it's not that we wouldn't enjoy it we just like we just don't there is a there was a a a a study where they looked at the most common reasons why couples get divorced the most common reason was contempt and the most common the most common reason for the divorce was contempt the most common reason for staying together was you admire the other person i hadn't heard that but it it resonates like resentment is just bad and i think a lot of business partners resent each other actually have you you've been in business with others i'm assuming yeah i've got the most i've had bad relationships i i'm currently in a very harmonious relationship with my c cofounder joe that i could see lasting a lifetime what feels different about it so when we first started together we we we we invested in startups together and we had a great time and he previously helped me with my old company the hustle i called emailed them and he was like hey if you're in new york tomorrow stop at the office and we could talk and i was yeah i'll there and like flew out there and like hung out with them and that's how we became friends and then we invested in startups together and then i was like i took like a really formal conversation with i was like joe i love working with you something i did with my wife early in our relationship when we were like thinking like hey is this something that we wanna like make real and like get married and have a family and i sat down with my wife and i was like let's just like walk through our life values and like what type of life do we wanna have and let's see if like they of a line and that's okay if things change eventually but let's just say let's just see if the direction is is is similar and so i sat down with joe and we said hey let's just outline like what sacrifices are you willing to make what sacrifices are you not willing to make what's a perfect day look like for you what are you driven by and like for example for me i was like you know i'm driven by ego like i it bothers me that people think i'm not good enough so like i i always wanna prove that i'm as good as i think i am or i'm driven by money i was like i work only forty hours a week i don't really wanna work more than that i'm not willing to sacrifice traveling i'm not i'm not gonna like get out of my house often if i have a family and he like named all of his things and we looked at the all the things and we're like how much money do you wanna have how much money do i wanna have we looked at all of the things it were like for everything that is agreed upon awesome for everything that's not agreed upon do we think that that's like a deal breaker and we they weren't and we're were like cool we like did a really good job of being very honest upfront about our wishes and now it's a much easier to address like any issues we have because it's like hey you he'll be like hey we gotta get this done and i was like yeah i but but he'll be like but you told me that you don't wanna like grind on a saturday so i'm not even gonna ask you it's all good we we agree to this things like that and that makes the relationship really nice is that we respect one another and we had those conversations super early on do you feel like the list or the conversations you had about that turn out to be true like are those really the things that that that you guys share together or is that sort of what you imagine you would share yeah for example for for the money let's just do the money one that's a real easy one we actually shared each other's personal finances with each other and interesting yeah we were like super transparent we're like here's all of our finances what matter like i would like to go here one day where would you like to go it's like alright well to go there we're gonna be like let's say that my goal is less than your goal let's hit your goal then and if we need to hit your goal here's maybe what the numbers would need to look like and here's what we'd have to make so like that's you know is that like something we both agree upon do you wanna be like we we're very transparent with each other that's wild i mean this is i know we you and i were talking on twitter a little bit about like how i'm super uncomfortable talking about money and you're like sharing your personal finances with your founder and kind it's it's interesting well you don't do that with your partner you don't do you don't do that with your partner like well you guys your guys is finances is are probably so tied together but you know they are tied together i mean yeah basically all of our you know essentially vast majority of our network worth is tied more business so we know what our distributions are and all that stuff but yeah we don't i mean we don't talk about that ever but it's interesting like i also like you're midwestern i'm a midwestern like i i feel like my my thing is like don't talk about it a while like it's ingrained in me where were you were you like that at one point or and did you change or i was always open about it because i saw my family like that and i was like that's so unhelpful for me because you're not telling me you're not giving me on road roadmap you're not i don't have anything to strive for because i even know what's it's possible my father owned a produce brokerage company which like it's like a small business but they sell like let's just say over the course of his thirty year twenty year career he sold like a hundred and fifty million dollars worth of onions but like i'm like how much is a lot of money is a lot of money like fifty grade a year or like three hundred thousand dollars a year like i i i have no i have no clue about this and so i and i always regretted that that they weren't open with me so i was like i'm gonna be open about it it's my my folks never talked about money i don't still to this day don't know if they're middle class wealthy i don't i don't really know kidding do you really you have no idea that's weird do support them i have supported them i i gave them a big chunk of money at one point but they they like regret took it they didn't really want it then i don't think they need and i think i'm gonna get it back when they passed so like they're not gonna use it you know they've always been very frugal we don't talk about it my dow entrepreneur work for himself like a small business owner he was a trader so he's traded stocks on his own he wasn't a broke i think he started out as a broker for a little bit but then he was on his own individual investor basically i think he did well for a while it didn't do well for while i think you know that's that's a tough road in a lot of ways he wasn't a day trader but there wasn't anything we couldn't have but we also didn't strive for anything that we couldn't afford it just i don't really know like eric's always been careful this so i i kind of absorbed that like just don't really talk about it and it didn't limit me though it's not like i i just felt like we we were everything was sort of fine is how it felt to me what do are you gonna do you're what are you gonna do at your kids i struggle with this like my parents never really talked about it we we don't talk about it but we certainly act differently than i than my parents are growing up you know we own a few homes you know we've a couple nice things so you know so it's like it it's it's it's kinda obvious that like we can afford things and do things but we just don't we haven't talked about it i think that's that's an incredibly midwestern in a incredibly more traditional older set of values my family had very midwestern values and i think a lot of those values are great hard work don't complain don't don't make people work for you like like i remember going like a restaurant and like we ordered a pizza and they brought us like a chicken salad and i'm like we're not gonna deal we're not gonna inconvenience you whatever else giving it like eat that exactly yeah that's like the attitude i've never sent a dish back in my life not million years not never ever years deal whatever yeah and so like i actually think some of those values are great i think there's many other values that are like i don't like using this word because it's too loaded but toxic bad there are a lot of values that are bad for example i think the stoic that midwestern tend to have that you definitely have i think that it's gotten you to where you wanted to go in a traditional success perspective but also like not being transparent with certain people i think i just don't want my family to be left wanting more when i'm gone in the sense of like i wish that they were more open with me for example i've not seen photos of my family really when they were younger or like i don't have any your parents i mean yeah my parents yeah my parents are young i'm like and i don't even know their grandparents name i don't know i had to do twenty three in me because i'm like i wanna ask them what my hair judge they was go we're white i'm like yes yeah okay but what flavor like come on i do some more and so or or i had to do ancestry dot com in order to understand like who my grandparents were like what are you guys hiding and i turns out i found out that and uncle is actually my grandmother was married previously and i'm like why don't you guys tell me this and they're like oh we didn't wanna bring it up you know like little things like little things like that i'm like that's weird just like just discussed it it just just just tell me yeah right that's weird so anyway i think that is actually bad though and i pray that i don't fall into that to into that trap and so that's why i with my family i've been overly transparent with a lot of things and i just think that that like lighten lighten things up a little bit i i admire that actually and and this this is something actually also admire about david i'm sure you wouldn't mind me telling you this david used to when we were in chicago when we had an office he used to drive to work in like incredibly fancy cars yeah and my midwestern sen is like dude don't do that he's like why not like my sense was like it just it sends a weird message he's right was he's like what's the message i mean everyone knows like everyone here who works like they know we're doing well like why why would i hide that from i agree with you that one by the way and and i i i it's so funny because he's right i think have you seen the big of le he goes you're not wrong dude you're just an asshole so in my mind i'm like i but i still struggle with it just because of how i was raised and how was brought up and and and and and the imagine the messages like the whole point is like i'm imagining that everyone's looking at that and i'm going what an asshole what it's like most people probably don't care they don't care they know this they know the score they're fine with it and if they're not that's their problem like david's boys is like if have a problem with me driving a nice car that's their problem not my problem like i've earned this i enjoy this car i buy this car because i i like the car i'm not gonna hide the car and he's he's right but i i just have a hard time with it still not anymore with it with him this is like way back in the early early years but but it's still is something that's in there there's a residual like struggle with that degree of honesty around money in a similar way that people like you know in america like who you vote for i i don't talk about what about it same chris rock has a great bit on that it's it's so funny when i say someone with the with a political bumper sticker on their car i'm like you're insane you're you're a crazy person yeah and they're probably like why i like this guy or like that guy or like curves like what why am i have to watch to hide my point of view and they're right too you know so deep down your point of view is healthier i still have a hard time with it not and that's probably my problem or may maybe it's not i don't really know i don't really know it's very interesting do you wanna change or do not care well i think the truth is my kids have at least my son who's older my daughter's five she isn't recognize recognizing any of the stuff yet but my son does and my son's really into like it seems to be into expensive things he like has this craving for expensive things so i mean he's gotta know what's going on to some degree he's not an idiot so i wanna sit him down and go hey son we've got this and we've got that and like i that isn't how i would handle it it'd be more like i've worked hard here's what we have we have some things we're gonna enjoy these things we share these things with friends this is not just our stuff and that's kinda how how i how i treat for example the house thing when i renovated a nice old house and and i make it better like it's our house but it's also all of our friend's house that free people are free to stay there as much as they want visit as much the have this property in wisconsin this old farm house a hundred sixty acres it's beautiful piece of land i've been working on it for years my friends use it more than i use i don't use it anymore i'm not even around there my friends can just go up there whenever they want and use it so it's it's about like we're fortunate clearly fortunate and lucky and a big part of this is you wanna share these things this there's there's you're not fortunate if you heard the things then there's something i think kinda wrong about it in from my point of so share as much as you can share this experience with other people and and and we're fortunate you know that's kind of how i sort of left it at this point i don't know we'll see the the the thing that i tell my friends and family is i try to let them know i don't i and and this is something that i couldn't grasp earlier on in my career i refused to admit this one thing which was luck is real and it has played such an an important part of any type of financial like just meeting the woman who you spend your life with like just the fact that we are in the same place at the same time luck is such a bigger component than i ever would have been willing to admit years ago and i think and i think that what i'll explain to my children is like look i worked hard but i frankly didn't work harder than many other people right i'm smart but i'm not that much smarter if at all than the average person the truth is is that i worked hard i had a skill but i got like fifty percent of luck was like was like part of that or maybe even more than fifty percent luck is such a huge huge component and i hope that i can put that on my family to realize that luck was real it just happened to work out because some timing thing worked out like let's say you started a business and you surged during covid you're like dude i just kicked ask or something i had nothing in which i did our business killed during covid i'm like i didn't know that was gonna happen that was just total lock or you know what i mean like things like oh it's it's absolutely real and i and i hope my family will understand that a hundred percent with you and i think it's way more than fifty percent i mean all the way back to you didn't choose your parents you didn't choose anything right you didn't choose your mind how'd you become the kind of person who is the way you are like there's a million inputs of billion inputs that you don't know about all the things what is it i don't regrets too strong a word but one of the things i regret most in my career is getting on stage at startup up school so this is like why comb startup up school years ago i forget when i was invited to speak i only invited once because i was pretty anti raising money yeah was i thought you're like the opposite of their ethos i i was but paul was kind enough to ask me to come up on stage and and give a talk but you and paul seem quite similar to be honest well i appreciate that i mean i i have a lot of admiration for his ability to to put ideas together and and think things through and what he's built but in invited stage and there was a question from the audience about luck so like you believe in luck i'm like hell no i don't believe in luck wow like and i was such a prick how early at mid twenties mid twenties i think it was when and i was just such a prick but a young punk prick you know kinda like and and and it's so embarrassing but you know like a lot of things are you look back on like poetry you wrote in college like oh my god i wrote that or whatever like what hurt is you know and and and you know it's like you just realize like that's part of growing up is is is totally misunderstanding the world and your position in it and then hopefully hopefully you get to the place in your in in your in your world where you're you develop a bit more and you have some self reflection and you can call yourself out on the bullshit that that you that you thought but also like that's who you work at the time and that's that's that last thing i wanna to ask you about was this staying off or staying up you said imagine all all the things you felt you were falling behind on if you didn't learn about them last year would it really have mattered if you started today instead watch out for the trap of must know now what's that mean right now this is like in the ai world we're in right now every once in a while like in my four you of feed in twitter it's like ten things you gotta know or you're falling behind it's like you if this this just like this everyone's falling behind meanwhile this thing is brand new and moving fast any human can can pay attention like i just keep seeing these stories about like if you don't know this and they're doing that and if you're not relying on top of this it's like no probably doesn't matter that much and all the things that if you would've have read that feed a year ago that you were supposed to know it it wouldn't matter that much if you didn't most things some things would be handy to know but like it probably wouldn't matter that much if you started now instead or waited a year in some cases one of the things i was doing for a while i'm not doing anymore but i should go back to doing it again this is actually easier to do during the pandemic was to go back and so so today is is is may twenty second twenty twenty four is to go back and all the podcast podcasts i listened to and listen to may twenty second two thousand twenty three so listen to podcast podcasts that are year old and during the pandemic it was great because you hear all these experts talking about this and talking about that and everyone's so certain of everything and you go back and listen like man we are so wrong about so many things and so many of the things we were worried about never happened anyway in this political issue and that political issue if this guy gets an office this is gonna happen if they get in off office this gonna happen turns out very very few things actually happened and it's really a nice exercise to go back and listen to old podcasts and old interviews of substance and realize that like there's some stuff that was right some stuff that was wrong but man the the sense of urgency in these podcasts is is so misplaced because most things don't need to happen right now you don't need to be up on this right now and you shouldn't feel bad about not being on the cutting edge of x y or z especially an edge that is re cutting itself and res sharpening itself every few months so that's what i'm saying i i try to stay a bit out of things i don't wanna be on the edge of things i like what what things settle in a little bit more before i really start to dig in do you read it any biographies a few i've wrote a few i i really love the idea biographies i have a hard time reading long books yeah and most tend to be very long i've got like a limit where it's like five hundred pages or less yes but i'll i'll do long but i'll do a long one once while but and i read a fair bit not because i'm in a competition it's just an hour a night is typically a book a week and great i read a lot of buyer i i like business biographies i love history so like a lot the world war two leaders a lot of the american like titans of industry a lot of just random people i i love biographies and i have this process of what i do i've got this spreadsheet where if i i only read on kindle and anytime i see something interesting i highlight and at the end of the book i'll like insert i'll create a timeline here's where they're born here's where they died and then anything that i highlighted that happened in this year that happened in this year and then what i do is i go to this website called newspapers dot com newspapers dot com has archive pretty much every newspaper ever back until back until like the sixteen hundreds and what i like to do is let's say i read this biography about ted turner ted turner the guy started cnn he was a fascinating guide to me or actually lando owner in the united states biggest yeah and he's done a lot of fascinating things and the reason why i used newspapers dot com is i like to go back to my kindle and my spreadsheet and i see alright in this year he decided that he wanted to buy land you know i'm gonna go read a newspaper article that wrote about him during that period and i'm wanna see what he said about his interests why he's doing it and like did he say like for example maybe he'll say like one day i hope to own like five thousand acres turns out he owns millions of millions of millions of acres and so i like to read what the predictions were as well as what the people were saying about the person at the time so you don't get revision history and what you notice when you do this is there's times that you'll read a biography and you'll think this was obvious that this person was going to do this or they're who wouldn't have predicted that this was gonna happen and or or here's another example world war two churchill was like basically he was like the the world's going to end like we are gonna die the world's over we felt that way during covid but if you realize a lot of history there's been many times where we have felt exact same feeling and we had this exact same prediction you know i remember i i recently read jfk book and like with the cuban missile crisis it was like the world's over and i go into newspaper dot com and i'll go and read what the predictions are and what you notice is that people are wrong more than their right mh and so what you're saying about things moving too fast i i i i read henry ford's biography about cars or i henry ford's biography at night so i interested in cars and i went and read like what people were saying in nineteen twelve when the model tea was coming out and like the predictions are just ridiculous and it's so funny that you don't to to reiterate at your point you don't actually have to be that fast to pounce on certain things it's really cut quite fascinating and to put it in perspective the ford came out with the model t i think in nineteen twelve or nineteen sixteen so the internet right now is something like thirty years old so that is basically like how old would you say the internet is or like the modern a day internet the the the commercial internet yeah like ninety five ninety six is when like you know really mozilla or nets kinda came out and really kinda made it happen it's basically basically it's older than that because it's just research thing but yeah commercially yeah thirty five years let's it's basically like a car company in nineteen forty do you what i mean yeah and yeah yeah and so what's really fascinating is to like read all these biographies and use newspaper dot com one of my favorite things to use and to see what are interesting predictions and how have they come true because i already know the answer but i wanna know what were they saying at the time and so that's my version of what you do with two thousand twenty three's podcast podcasts i love that that's i i didn't know that site existed too that that's fascinating it there's an x account i follow call like pe archive or love but i love that one it's a great it's a great one to follow and just you know like and and the thing is the thing that's a little bit interesting about right now the time we're in is it there's so many people saying so many things all wearing the expert uniform some people are experts like live there are experts in this world but many people act and play as one based on just their ability to communicate on platforms and there's just so much certainty layered into their suggestions and requirements and requests and demands but it's just it's very healthy to go every time you see that every time there's like a you must i i always buy have and go probably not like the more forward they are about being certain and right about something sort of the less interested i am in the short term and i'd rather just sort of stand back and see how it all plays out and at the end of the day you know there's there's plenty of opportunity in a lot of different areas you don't need to just pounce on everything as it's happening and in many cases it's it's best to wait a little bit and see how things settle up i mean i just think about like with ai like all the companies that began to implement ai stuff early on and and then open ai is just like wipe them out in lot of ways for a lot of different reasons and when you build other people's platforms you're very very much at risk of things changing t plates shifting very quickly you might have been better off waiting and seeing how things shake out so anyway who knows i wanted you to come on here and just talk because i've read your work for years i've been a fan of yours for years i've seen you do a bunch of interviews and i just wanted someone told me this guy named dylan just said you should just ask people what's interesting to them and that's what i wanted to do with you because you're an interesting person and i respect your opinion on so many things and i appreciate you just coming on and just r with me and just tell me what's intriguing to you and it's been a lot of it's been very valuable for me just to see how you think and what what grabs your attention well thanks for the invitation it was it was really fun and and as i mentioned earlier i just i i wanna make useful things and hopefully this is a useful conversation for for us and for anyone listening so thanks thanks for inviting me and it was a real pleasure alright that's a pod i feel like i could rule world i know i could be what i want to put my all in it like a days off on a goal less travel never looking back