I dropped out of college and built a $3.6B company from scratch

know what you're getting into here nope let me give you the simplest text explanation you know how on twitter you're funnier than the smart guys and then smarter than the actual funny guys we did that in the business podcast podcasting space i feel like i could rude where to know i could be what i want to from at all in it like a days off on a goal less travel never the way i was supposed to be prepping for this podcast and in the last hour actually all i did was watch millionaire match maker season three episode eleven which aaron if you remember is when your c founder went on millionaire match maker and so i don't have a whole lot of prep but that was a great episode would do you remember when he did that i do yes we're were you in support of that not exactly so it was we we took a flyer on that one they actually well the the weirdest story was they asked for both of us to do it somehow i had better judgment so sam have you seen this episode yeah but so i actually met your c founder dylan i was starting my first company in san francisco i didn't have a lot of money and we weren't making any money and i did part time work at a scavenger hunt company and box was a client one time and so i got to hang out with him and he had told me about being on the show wow really and by the way we were like at this bar at like the end of the scavenger hunt at like seven pm and he pulled up his laptop and went to the back table and was like working and he couldn't enjoy the scavenger hunt i think that's one of the crazier things about y'all store you've been there for twenty years is kinda like four friends you know started in college type of deal and are all four still there now twenty years later so three of us went to middle school and high school together than four of us went to high school together and we had tried lost of different ideas throughout middle school high school and then finally as went to college kind of people people split off to different schools and then this idea kind of emerged and we all we all kinda got back together on it and then dropped out of college and in kind of two two parts in two thousand five and and two thousand six and so we we've just been working together for for i mean honestly like almost thirty years on different things which is kinda crazy to to think about it at this point so right now we have dylan is you know cfo he runs a bunch of functions in the company he was famous for millionaire match maker apparently definitely is his main claim to famous at this point and then jeff and sam jeff has a bit of a a farm he's he's kinda getting into the farm world and then sam is at philanthropic and on on claude cloud code and we he now is a constant thorn on my side because every every three days somebody says the cto of box left box to go to philanthropic but he actually he actually retired from box like six years ago and but it causes like you know sort of une ending viral fodder on that one that's pretty incredible that you can found a company take a public ever you go and work at and philanthropic at isn't isn't the instagram founder another foundry founder instagram i mean they they have their credit they've done obviously an insane job on recruiting so i think it might literally be a requirement to have been a cto of a like a public company to work there at this point but like they have like this like like there's like a list of like ten of these people you know mike's over there obviously now with andre you know sam on our end built you know some of the most important software and infrastructure that we run on to this day so he's you know he he's obviously a huge asset for them but you know they've done an incredible job at recruiting dude is it true you so you've been doing this for a long time and the the idea for box i think was pretty simple like hey you should be able to access your files on wherever you are not just on one computer i think you guys started consumer and then is it true there was sort of this like fork in the road moment where you you you guys went enterprise and like you know kind of the cofounder had to debate it out is that was that how that went down yeah i mean it's it's always sounds way more dramatic you know in when when we kinda compress it into the in the brief story but it was a multi month period of of kinda like your classic wandering period that all startups kinda deal with where you don't know if you're gonna pivot you don't know if the business model is gonna work you don't know if you're gonna get your next round of funding like some things are are clicking and working some things aren't and we had started i would say not even as a consumer or enterprise we kinda started as agnostic to who the user would be we just said hey you know it should be there should be a secure way to access your files from anywhere like it was an obvious idea to us and then what happened was it started growing but consumers where had this where had this kind of you know very straightforward fork in the road consumers wanted to pay as little as possible and they wanted a certain set of features that you'd have to go and build enterprises wanted to pay a lot more but they would need like a hundred times more features and oh as we kind of like thought about like well who do you focus on we did eventually kinda conclude you know something really obvious in retrospect it and and i can't like un see it as they look at other people's strategies over time these were just like totally different markets like the enterprise needing to securely manage their most important data as an organization would require us just a completely different set of functionality than what a consumer would need to back up their photos and and access their music from anywhere and those were just different markets and there was different business models one would pay like five dollars a month the other would pay maybe five million dollars a year and like completely different business models different markets different teams you'd have to build different products you'd create so we did eventually run into you know effectively a fork the road and after a few months of of kind of debating it out and assessing the opportunities and you know people people kind of having you pretty different views on what to do we eventually pivoted you know kind of very forcefully into the enterprise we we you know almost burned every every boat other than a couple that that we we want we still wanted a freemium model in the enterprise we wanted you to be able to sign up as a as a kind of knowledge worker but we we very firmly wanted to make it an enterprise only business model and i was actually the most reluctant and the last one to be convinced to pivot so kinda credit to to the other founders and and some early employees that i think had more conviction but once we had once we collectively had conviction that it was it was very straight forward one one thing on that that decision enterprise versus consumer dropbox obviously i think do would you say they went the consumer route initially or no because like you know can can you look back now say oh you know one's a this billion dollar company i think dropbox like i billion dollar company you guys are just under four like in retrospect now that you got the benefit of like seeing it all play out was that the you know was that the right move or or is that overly simplified hey everyone really quick if you're enjoying this episode on ceo stuff so del heavy hard conversations with your team hiring then i've got something for you so the team at hubspot they actually went and put together a bunch of best practices that sean and i use in our own companies and they put it together and something that's really easy to read and understand and so you wanna just save yourself ten years of headache and heartache then you should check it out i wish we had this long time ago would help me a lock but there should be a qr code on your screen that you can scan or a link in the description so check it out it's totally free and totally awesome well it was definitely the right move for for us and where we were you know the way we kinda did the math was google had to own the consumer you know we we saw the g drive kinda writing on the wall they would wanna bundle it with gmail and most consumers would would sort of be satisfied with that and then icloud i'd added on top of that and then onedrive and so it like the consumer really looked like a total kinda death fit and dropbox i would say performed far better than than i would've have estimated if if from just a pure like economic standpoint i would've have thought that the comm monetization would have been much more impactful so huge kudos to them on their execution and and just know obviously building a world class product on that front what we were very clear on was was the only way that we would not go out of business was by being enterprise because we we just were we had we were too convinced that over enough time that the consumer space would just be too competitive and too comm monetize so not only are we you know fantastically happy with with the the decision but i think it was the only outcome that would have would have produced really any any form of success and then i think over the long term like let's just say we had another ten years to the timeline i think the only way to build a very large business as an independent company in this category is is by being enterprise focused just because like you know where most dollar gonna go for managing data securing data yeah you know kinda caring about how it's governed in in a you know in a in a workflow it's gonna come from businesses and so and there's actually you know i think relevant lessons as we look at the ai space is i think most dollars in ai will eventually be enterprise dollars there'll be some you know there'll be fantastic outcomes in consumer no question because there's you know some ways to to build consumer businesses out of this but by you know by and large where's intelligence valued it's gonna be in the enterprise so just as where software valued it's it's in the enterprise and that's where where most dollars of of technology go and other than you know three companies that make money on advertising in in consumer tech you're fun to talk to because you're only a few older than sean and i we're thirty seven and thirty eight but i feel like you're so much further i mean when when we were both like you know nineteen or twenty one years old you were on the cover of magazines and you were like the poster child it was like you and kevin rose was like you know you could make it for for me it was actually the thing i was obsessed with was when we moved to we dropped out we moved to silicon valley and like if you remember like you guys would have been just too young maybe like seventeen eighteen but like it was like sam alt was with looped was like top collar collar yes that was that was the person to be in in in the valley i mean other than you know z it the same by the way i think it's the person to be again twenty years later well we like grew up a little bit like watching it it's really it's been always really fun but i heard some crazy stories about how you got offered all this money at a very young age to sell the company and i always put myself in that position where i'm like what would i do and of course like the reason you are you and i am me is because i probably would have taken it like yeah like i wouldn't have had the po like in the like you have had but how old were you when you start first started getting acquisition offers and like can you tell some of the stories of what's that like to be such a young person and like facing like like this life changing amount of money sure yeah well when we first started we dropped out of college it was four of us living and working in berkeley and we got a call from yahoo and it was the corp dev team at yahoo that had basically the the team that had more or less just been responsible for for buying flicker so that there this product that was like in the late nineties early two thousand's called the yahoo briefcase and it was it was sort of one of our predecessor so it was an online storage you know kind of product but it was like you could store maybe like fifty megabytes of of data in the in in yahoo briefcase and for us you know we we had finally achieved a gigabyte of storage that you could have on online and we were like the modern simpler faster easier you know kind of more up to date version of of yahoo briefcase so we got called in by by the corp dev team and for us we were like holy you know shit this is the biggest moment of our lives and we were like debating like what acquisition price would be we would we be willing to to take and i think like probably the most we could have ever imagined was like five or ten million dollars and we were like you know that's our price we'll we'll we would definitely take five million you know was it like alright on three everybody say number out loud one two three seven million i think i think we we didn't even have enough we we probably thought we would jinx it if we even did that so it was more like a very serious discussion so we we we drove down to yahoo corporate headquarters in a nissan minivan that was like totally breaking you know falling apart and we we we did a serious meeting we presented our whole strategy and you know we we went through the the product and i don't know i i don't remember all it's very hazy but like out somewhere on the order probably two weeks later we just got like an email saying it was really nice meeting you guys thank you for me why and and we had done all this build up in our heads of like what what would the number be that that we would sell the company for and and again any of those numbers we would have been the just ecstatic about taking so it's it's one of these things we're like you know it it we we we have turned down offers but we've also been in situations where we totally would have taken you know that that very early offer and just taken it off the table and then you know later as we scaled because we we've had we have we've had every problem thrown it us we've had rounds that didn't happen and just like totally busted rounds we've had a be bridge loan by our investors twice so there are definitely you know there definitely you know parts of the of the journey where we would have you know if anybody has shown up with with any offer we would we would have accepted it probably and then it's you know as these things go like when people do actually show up for offers you get you you're like you're your your chemicals in your head are totally different and you're like like oh my gosh like we just gotta keep doing this and so probably the most classic one that we faced was a a very kind serious interaction where where we would have you know been i think quite happy about the outcome on any kind of financial measure but we looked at the situation and we were maybe our our mid twenties early to mid twenties at the time and i think this is now like well documented by by a bunch of people but but i i think it kinda just happens probably pretty uniformly which is like you just you like if you really deeply process it in like in a very intellectual sense and you're like okay this much money like this is super interesting you know etcetera and then you like start to play out like what am i gonna do in two years from now or five years from now or ten years from now we basically just process like we would probably be doing something just to get back to exactly where we are now like there's there's it's unlikely that we're gonna work at this new company for more than five years each like so so that's not gonna happen because everybody every one of our friends that had gotten acquired had already left their acquired companies so like that was probably not gonna happen so then you just look at it you're like okay well you're probably trying to do everything you can just to get back to this exact situation but of course you have more cash that's that's obviously positive but but now we're in this situation we've already defied all the all the odds of of getting here in the first place and all the things that kinda gotten in our way like why don't we just continue to double down on this given that we still believe the market is still a hundred times larger it became this very kind of calculated decision which is what's the amount of of kind of you know how big is this market still ahead of us we thought very large do we like our kind of compounding kind of you know approach where we think we're getting better every day every week every month at at at our product and or strategy we know that there's gonna be a lot of headwind and a lot of of severe competitive pressure that we're gonna face so it's not gonna be easy and then it basically just came down to like you know that the kind of base and regret mini manipulation and framework of like of like what thing are we gonna regret more or less and we we at least we convinced ourselves that we would more regret not continuing and just seeing the next set of cards and keeping on scaling more than we would regret you know sort of turning down this offer and having this start over i don't know if it's actually true like what would we've really regretted more but but that was the decision it always got wrench like we did an off offset with a four of us and old for you guys and how much was the offer it we were in our mid twenties so probably two of us were like twenty like twenty five twenty four or twenty three and we we don't really talk to specifically the offer but but you know call like in the half a billion range it's basic and that's and were you guys taking secondary along the way to kind of at least have the have some some of that regret motivation if it all blew up that like at least we we got you know a safety net here or no safety net not safety at levels of of secondary so this is a very different time period in the valley so this was you know very early two thousand tens and secondary was not neither in fashion as much as it is now nor were the amount of capital the the the same level so so i think it was like you know people could you know feel better about the apartment they were renting as opposed to like we're like good on the decision you were like the tito ortiz of tech like tech you know like you know the early you guys they got paid like a thousand dollars to show up at a five hundred dollars if they won and like they like made it popular at a dollar you like you accept there they're like being honored in the the hall of fame but they like can't see or talk the left side of their face anymore right i honestly if there's like any analogy that works for my entrepreneurial life it would be that so but we we we have had to grind through every every worst practice that that you could that you could imagine and and i mean we've lived to to tell the tail so you you have a pretty insane investment portfolio too let me see stripe fig robinhood air table insta cart plaid like that's a a pretty baller portfolio might be there might be some hallucinations on two of those okay maybe chad lied to me i i think i i may i there's some good embedding space clustering of some of those brands unfortunately so i met dylan field in the seed round and what what a lovely what a lovely character and kid did you send him an nice to meet you email like a yahoo to him yahoo i i i think i was i hope it was like three percent better at the follow ups but i met him and i did not have the creative imagination for what he was talking about and i obviously should have because i believe in cloud based software for everything and he was like designers are gonna do real time collaboration on stuff and i was like i don't know man like we we we we kinda make images fine so i was like very like i was a a huge on the on the pitch and definitely to my detriment but unfortunately that would be that be a so i didn't i didn't get on fig my early enough but but few of those yes has the what what's worked out better the box equity or the the angel portfolio equity are we getting close or because like for example we have a the podcast got bought by hubspot and da mesh from hubspot comes on a bunch and he made a huge bet into open ai and we're were like dude you're gonna make more off of that than you did in this like thirty year odyssey of hubspot i like can probably i for fortunately at least for for other other factors box box is still ahead but that the big thing i should have done is hedge on all of our underlying suppliers we're like one of the biggest customers of like sea gate and western digital and and so like we could see the stack that you would need for all of this and and it's i don't know if you guys have watched like the sand disc stock but like this is the the just the most insane you know is just set them stocks for for these guys i don't know what you guys are talking about what is sand disc is like an old the memory stocks have gone bananas right is it sand like a like a eighties or seventies sand is up about what three thousand percent maybe in the past the two years i remember sand they made like flop right they they they made everything and they i mean we probably wouldn't exist without sand so usb thumb drives were like one of the one of the catalyst for okay we should just like move that to the cloud so if you just bought santa's stock that like on on just because you were really into the usb thumb drives you would be doing fantastically well right now have you seen any cool so you you're talking about like the the companies that have gotten big because you've been an the ecosystem where they've been customers or you been customer customers what else did you see early on because they were there were customers i mean way more than i've invested in but but you know i think if you just looked at probably even our own tech stack over twenty years and you just you just bought the stocks of what our tech stack represented like that portfolio alone would be you know you would have you would every every index exactly and that's actually i mean that that's sort of generally a phenomenon right now in in the valley which is you can kinda just see like you can generally see like what what are the engineers using and that tells you quite a bit about the future now there could be some mis misread in the signal there but i would i would say within ninety percent accuracy it's it's gonna get you like most of the investment advice you need it's a pretty underrated strategy i i call it investing in your p and because you just go look at the expense items and like i learned this when we were doing a tech company same i like oh pager duty an elastic surge and all all these compass slack know we were one of the first hundred teams on slack or something and you know our shitty started idea it didn't work but like we we sure did identify a bunch of really great underlying tools whose ideas did work i own an commerce business and e comm is a pretty brutal industry like pretty low margin type of business but i just funneled all the profits into shopify and the underlying like e commerce stack and i've done great you know i've made more money there than i did in the the actual business itself but like i also wouldn't have understood that ecosystem and like who you couldn't pay me to switch off of tad i not like gone through the pain being there yeah i interesting the the the funny thing is like this data is basically out there for every investor and and i i do think that the it's probably not kind of leveraged enough but yeah i mean most most of the best practices are just well known by engineers very quickly that's a really challenging thing to think about sean when you you're like well i have this business that's like a small business that's probably gonna grow quickly but then you think like i could somehow make more investing this already big business and your head you're like well once it's it's incredibly matured like it it can't like grow more like everyone has that story now originally it was uber now at spacex and we all could have invested at in spacex when it was worth eighty billion dollars and you're like this is insane no way did you see there was a a slide deck recently like i think c two put it out or or they did this analysis which was yeah going from oh do you do you remember the exact was like one ten thirty hundred billion to a trillion than ten billion to a hundred billion i think yeah you're like more likely and you get there faster it's like oh i you know i i some of these things though are a a little bit tough simply because we are in a you know we're we're in a a pretty kind of fever environment so it's always hard to like how do you normalize for the particular multiples that we're seeing and and and is that like a sustainable investment strategy versus right now we're we're in a moment where that is is kind of working when you look at it backwards but yeah that that was that was definitely counterintuitive when i thought hey let's take a quick break you know that feeling when strategy is done the brief is written everyone's aligned and you realize someone still has to sit down and actually create all the content that someone is usually you and it's due tomorrow well the breeze assistant from hubspot can help it works right inside hubspot you can draft campaign copy blog posts emails all in your brand voice all using your actual customer data so you don't create just content you create content that converts check out hubspot dot com the agent customer platform for growing businesses you you have a couple other kind of contra you know you have a good answer to the peter teal question of like what do you believe that few others would agree with you i'll read you a couple of them you know you're basically like bullish on the job market i think most people think with ai all our jobs are gone you're like no bullish on the job market other people think with ai we're all gonna be working less i think elon has said this and a few others like you know you know hey here comes the four day weekend every weekend or something you're like no we're gonna be working more and that software companies like these saas companies are gonna do well so you know jobs work hard work and and software companies three things that most people i think feel pretty bearish on you have a different opinion you wanna give us your take on each one of those you know so so much of the idea that jobs go away or that we do less you know has to come from a place of of effectively your short just human creativity and ingenuity and and the idea that there's sort of we we don't have an ass appreciable appetite for for more and new things and i've just seen very limited evidence that suggest that we don't want to go and discover the next cure for the next you know you know niche problem that that people have or the next new form of entertainment people want to experience or the the next new consumer product that that people wanna go and sell or the next you know new new podcast podcasts that that wants to be created and so like if you don't believe that that's gonna happen then sure then you would basically believe we have that that abundance sort of comes at the at the expense of jobs and of us you know doing things and so so that that theory has to be that basically you know the agents are gonna do all of the all effectively the useful work which then frees us up you know so much that there's really not much else left and i just think we will find a way to create a ton more work for ourselves for better or worse like my it's not obvious that my my view is is particularly like utopian like i think does some make extent you elon elon vision to his credit is actually a far more utopian one than the boomers it's actually funny like they because they believe in the same underlying technology trend so they base basically both believe in in if you extrapolate out to ag he then the boomers believe that destroys us and elon believes that that we get this utopia where everything is just done for us and i kind of and more just until proven otherwise i just in a third camp which is like it's like the same progress of maybe both of those two but with more of a pragmatic outcome which is like we use that technology to just then create a new set of needs that we have to go in all all kind of support and fulfill it's just like a very long list of things that that the world is still going to effectively value like the world is gonna still value in person education for children they're gonna value childcare they're gonna value going to a restaurant and having you know human interaction they're gonna value going to a show they're gonna value like talking to a financial adviser that that appears to sort of you know have some sense of the market and your set of needs and also has ten other clients that they can kind of like triangulate with or you know attack professional that you can just like you know is like accountable for if they get the thing wrong like their jobs on the line versus like an agent that that can be just shut off and so that's you're not really sure what what accountability they have so like for all these reasons like humans just stay in the loop and so i just think we end up having still a lot more work for everybody to do i would say in the four hour the four day work week thing also kind of suppose something different which is you you basically have to believe that that assuming that anybody in your in your sector decides not to do a four day we're work week then that company you know with with the power of ai will get twenty percent more or twenty five percent more output than new will and so which market is gonna basically have some kind of like collective agreement that says no our category everybody in our industry is only gonna work four days a week so it it's just like it requires such a collective sort of like agreement on on the part of everybody that that you wouldn't then just like have some actor in the system decide no i'm just gonna like i will just ship more software i will sell to more customers than you do which then gets everything back to to five days a week so that that why is like just very imp for that outcome to to really exist so check this out there's this book sean you'll like the name of this title it's called how to live on twenty four hours a day and it's a book written in nineteen o eight you guys should read it it's really cool i just got it and it's all about what happened after the industrial revolution and there's this huge burst of of white collar jobs and there's now millions of americans as well as europeans who now are not in a factory anymore and they're doing these white collar jobs and then there's all these like house waves this is in the book and they like they're like well now i don't wander our clothing with my hands i use a machine and i have all this time and the white collar workers are like you know we have extra time and they're all ask themselves well if we have all this extra time now why do we feel busier than ever and the whole book is how to make sense if like how to like make your twenty four hour day how to get everything you can out of it and it's a little bit of like a productivity book on the busier than everything i mean it's every startup founder you've ever met right now absolutely is busier than ever like they're way busier than than we were when you know be before ai and the reason for that is because ai it's sort of like this deceptive technology because it like it lets you get started on so many things so easily but then you start have to complete all the things you started and so you know you you think that like i'm just gonna deploy all these agents and then i'm gonna like go to the bar or go hang out but like when the agents are then done somebody starts to be responsible for like what do i do next with that information what do i do next with that piece of software what are i you next with that video clip that got created like all of that becomes human work again so so like i think every every single person that is like the most ai pill right now is just they they like we're just drowning in work because we're like kicking off way more work for ourselves and we we can't ever get off that treadmill because of how easy it has has become to just create this work like i don't like an hour before this call i kicked off two you know kind of processes that now i i didn't even need to start but i started them and now i'm gonna absolutely add another hour to my day because i'm gonna go and like like do whatever whatever the agent i'm gonna go and follow up with all that work like and i didn't even have to but it was so easy to kick it off that now i've created more work for myself so we're just going to do that for everything here here's the one thing you're missing you didn't name it this is your j paradox this is your chance to live on for the next hundred years we need le paradox is basically the easier it is to do work the more work you'll do and the more tired you'll be at the end of every day yeah i i i mean if we wanna run with that we can we can we can leave law dog come on formal we always as we'll get an a in there yeah so i'm make it a law are you are you so you're working your ass off right now i am yeah it's insane we had rep ceo on recently and he was amazing and he told he told the story sean like that's a real thing anyone has ever said it was kinda funny but he told the story about how before they kinda took off they're kind of a no man's land or even failing for like a handful of years and everyone knows this slack message or this text message where from from an employee that says hey can we talk and i was like i got like one a day and so everyone was quitting and like my nervous system nervous system was just crashed yes yeah and i and we all go through cycles of that but how has your nervous system like kept up doing this for twenty years because you've had some crazy should happen i think that you had like a hustle takeover attempt you said you've had all like these bridge rounds happen i mean you've like been through so so much shit and i would assume you don't need to be doing this anymore how has your body handled this well i don't know if my body has handled it but but i'd say my from a brain standpoint it's very very stressful i e see a therapist just like to help me like call myself down from an anxiety standpoint you know to i'm you know kind of example like those are like the worst slack messages there's like if you just ranked to all like all of the all of the stressful things because you're just like like you know there's like forty implications when a when a he person leaves that you then have to like like instantly kinda cycle through the probably the reason i keep doing it is because the upside still exceeds the the anxiety and the stress the stress and and kinda time cost and but what's your upside it's not money at this point i would have to imagine what what is it the upside is is the you know for lack of any better explanation is just like the intellectual curiosity and excitement of building something and then having that thing be used in the real world and knowing that like you know you you get to just move that forward another another step and then right now i'd say it's even amplified because most of the technology that that is being built by everybody else ends up being something we can also build on top of so it's like there's an une ending amount of things that we get to go in and and kinda play with and and be a part of so you know if we were doing exactly the same thing every single day and it was it was totally a grind over like you know i could probably pull that off for maybe five years i don't know that i'd be able to do like a decade of that but like i could probably put in five years or just like total grind but this is you know a grind plus s shi adrenaline because boom new model drops what's what's the implication what can it do you know how does it touch you know well for us we love it because it all needs unstructured data and the the information that that we get the store and and manage and so whether it's you know the new models new agent work you know what's happening in the landscape there's just an unlimited amount of of things that you can kinda bite into and that makes it very exciting and so have you almost quit when was the time when was the time you were closest to bailing i would i would never like personally bail so the bail that that could exist would be like you know you you kind of sell the company or you like get fired but you don't fight it you never thought about resigning a ceo there was a moment like nineteen years ago where eighteen years ago where you know am i like a ceo or am i like a product person and then do you have to get in a ceo and and then what we just solve that by getting a coo and then i was like oh god this is in like there's some like god god created a role for people like me where like somebody who like wants to do operational stuff gets to do that and then i get to still do product stuff but also be ceo i was like holy crap whoever came up with this idea like is brilliant and and so that from that point forward that sort of solved any kind of like like you know self doubt i had around like my operational skills and then the rest has just been like you know is the company gonna work and then do we need to view the company in a different direction or not you said you go to therapy sometimes and it's been helpful what's been an unlock you know either maybe a a realization or a is there a win that you could share early on in therapy i kind of it was we just like identified i don't even know if there's like a word that everybody uses or only because like i've been going to therapy before like chat so i didn't like research everything that you were ever told but like she was this term customization or cap and so like maybe that's like a well known term i have no idea but the the theory being that like i things so like like you know i get one piece of news and then i instantly extrapolate out like the worst possible outcomes like there's one person leaves which means the entire company is out of business because like you know they leave and then they were gonna miss this one thing and that's gonna stop working and then that's gonna break and then and then you know doom and by the way i think actually like most people most ai boomer should probably see a therapist because it's all it's all just catastrophes so for me like what i basically just just started to once i could like kind of like maybe like understand it and and like name it as something you can feel when it's happening and then you're like you know what i know this is i've seen this twenty other times or fifty other times in this category and guess what it doesn't mean the end of the world the thing doesn't end up blowing up and doesn't break everything you do recover and so that sort of shorten the cycles of the like anxiety pains because like previously it would be like kind of like you might be like knocked out for like three days because you're just like oh my gosh this is the end this is the end of the whole thing and and then you you go through it enough times and you're like okay this is like totally sur survival and then sometimes i i almost like i and now probably like a little bit bipolar on it because like half the time i will just downplay then when something bad happens because because i just i like i i don't have like a hundred percent intuition on like when to like what level to toggle it so then for other people just be like this is totally fine we're gonna be totally fine is not a big deal and it's just because again i've like i've i've sort of prem mitigated the catastrophe and then other times i you know i i then still let it loose a little bit but that's probably that one of the best tools i've i've i've been able to have we got to do a thing with ray dahlia last week and he had us do like these personality tests because that's one of his his kind sticks i'm like a ninety nine out of a hundred on being neuro and it bothers you you're not a hundred yeah i stand up on that i'm like what what questions are this i enough but i i think it's like i'm i'm it's probably jagged what i'm actually neuro neurologist about i think there's only like five things i have some like like you know my the most common slack is usually just like this something three pixels off and i was just like going through our website and i and i just like like i it got stuck in my head thanks podcast guest is brought you by my friends at mercury they make the world's best banking product i think you know this already i used mercury for all of my businesses i think i have like maybe seven or eight businesses we use mercury as our business banking across all of them and now they actually just launched a personal banking account so i have my personal account there i moved off of wells fargo in chase i'm just all in on mercury why i like products that are easy to use i like products that get me and the problems that i have so like very easy to make a joint account with my wife very easy to spin up virtual cards one click and i get savings yield it just has all the stuff that i need in one place so if you're looking for the best banking product on the market it's definitely mercury i will fist fight any anybody who dis disagrees me on that go to mercury dot com slash personal and learn more mercury is a fintech not an fdic insured bank banking services are provided through choice financial group and call them an a members fdic are you a believer in these personality tests the way dolly we've had actually a bunch of really impressive successful people come on and almost and very much swear by the kind of personality that stuff which i had always just thought is horoscope like that's cute you wanna crystal too like get i didn't not i didn't really believe and now i'm like i i think enough smart people have to have to have told me this where i'm like okay i should probably reassess my my my jokes here who else is into him besides ray we had who was the other mu ish was on he he's you know an investor i think is he's very very smart he was he's he described how his life changed from a you know an assessment that that told him like yeah hey the reason you feel the way you feel is because you're playing a game of managing clients and people but you actually thrive in solo player numbers based competitive games and you know he when he was switched to investing he like thrived because that's exactly the type of game that that rewards yeah do do you believe in him i probably veer more sean's and prior to to his ray interaction i i think it's like fun is like a it's usually like always like a good ice breaker at a at a corporate site right i've i've rarely left being able to do anything actionable about it like yeah we know you're red like we we we know you're gonna be aggressive what what are we gonna do about that information we know you're collaborative like it's very obvious you're collaborative well some people use it for hiring they they make you do like there's a whole company called culture amp i think it's called where you where you enter you enter the job that you need to hire for and it tells you what personality type and then you oh have your trans does like a hundred million a year on their their yeah so but like i saw i i end up somewhere just in this like i'm told i'm fine with it i'm also like i i don't run the business on it like how i talk about people who are religious yesterday you wanna have your religion like we're good yeah seems like it helps a quick different question kind of the in the same vein of kind of know thy myself from what i understand you're pretty big like business strategy nerd i've seen i've heard that you've read books until late at night and you've you've been do this for a long time you read books yeah how one of those guys you know when omni job came on he's twice he's referenced like the to call like seven powers or five powers or have have how many powers there are of def seven alright seven yeah are you if if i was to ask people who kind of either founders you advise or people you've worked with if i was like y what are errands kind of like the frameworks he really like pulls a lot or tries to like get people to adopt what what are some of those that that you could help teach us yeah i've read every book so i i have a pretty good i have a pretty good i i i believe i have the best set of books at this point this is something that i'm it's like one of the rare things i'm like over confident about if founders only read seven powers it just do seven powers it's all that's like obviously good but if you add to it you repositioning if you you know this one love positioning nobody reads positioning repositioning and then they up their whole market positioning strategy so what seven powers does is it he's abstract basically seven other books in a very compelling way and everybody should read seven powers but if you don't deeply understand innovators dilemma and this other book innovator solution it's like this great tandem yeah they only do give you the problem they don't i've never really i they even don't know there's some innovator solution it's i mean he knows how to sell the the you know sequels and so this so innovator strikes back this the trilogy well everybody everybody gives up they'd ever read the solution because they're already like three hundred pages into the dilemma and they're like oh my god so so you you wanna read both the the dilemma and the solution in tandem like back to back you wanna read some powers you wanna read positioning you wanna read you know for it's a little bit more on the fun side but blue ocean strategy it's good kind of like mostly academic plus some a little bit infotainment and then you know maybe like crossing the chasm or inside the tornado so if you if you had the time and you could be like locked in a a a a room and read like six books if you if you read that you will be able to predict a hundred percent of things that happen in technology like without fail like you'll know every competitive move that people are gonna you'll know why markets do the ways the the things that they do you'll understand so much more than just trying to like like wing it and guess what's gonna happen next do you have like an anti read list where you think these are popular and people read them but they're do you don't think people should yeah well there are some kind of like your your kind of like classics in like leadership books that i i have not found myself getting as into but i i do appreciate why people get into them it doesn't like trigger my same sort of visceral you know kind of re reaction i think that that they're intending you're not you're not you're not a leaders eat last or a stretch with life type of guy make your bed yeah i'm i'm i'm not gonna you know i because i respect the the trade i don't wanna i'm not gonna call on anything specifically maybe offline i'll i'll mention a couple but there are there are a few were are like i'm like fifty pages in and i'm like i think this is kind of like a little bit too tight is that well let let's use this because right now it's easy in hindsight when you read the books because they're like giving you a case study from fifteen years ago twenty years ago and you can sort of malcolm glad like revision history your way into like yep any conclusion those are the fun ones of you know the ones that were written in like you know ninety three and it was like you know digital equipment corporation will be the largest company on the planet based on you know and it is like it died two years later right so but but right now there's this fog of war with ai and it's there's basically game of thrones you've got like elon the king of the north he's coming down he's trying to make it happy you got the ant i guess how do you see this playing out once once you think about like seven powers positioning when you think about some of the frameworks you have do you have any predictions for us that you can look really smart on or dumb on in next seven years i'm glad you asked because it does i should i should based on my confidence on the power of those those six books i should be able to tell you the answer they did not anticipate the ai market just the record i think said if you read these books you could be anything with a one hundred percent of hit rate all the time but go ahead yes now you just said i don't know no idea who's go well good partly because there's other factors here that that a a try didn't write about so he didn't know whether china would win in open weights models no i mean there are literally other factors because we have government like government is such an x factor in this china as an x factor so no idea on on these things more what these books are good at is like it will will it'll be if you're an entrepreneur it'll tell you if your idea is gonna be remotely you know gonna work or not i so it it works better in kind of like early stage like like will this company find a category that it can like wedge into or will the incumbent more likely take the category like so i use like innovative dilemma and innovative solution as a as an example we'll we'll we'll basically tell you seventy five percent of the time whether you have a shot as as a new startup yeah can you make can you can you me give an example make it make it a little more obvious yeah i mean like like the the whole point of innovators dilemma was everybody kind thinks it's like a tech disruption book because it's like oh this oh they got disrupted by a tech or something but but that's like that's it's too simplistic the the key is what innovators dilemma tells you is if the business model is not something that the incumbent wants to pursue because the business model is unattractive to the incumbent so if you look at it through that lens it will very quickly tell you like if you have a new startup up like does the incumbent is the is the incumbent gonna find that business model unattractive or not and if it's unattractive they won't pursue it and if it is then you very much you know need to assume that that incumbent is going to try and compete with you then you have to decide is that a technology that that for whatever reason is like a sustaining technology that the incumbent is gonna be classically good at or is it like so hard for them to figure out that they're not and then that tells you things like google is gonna obviously get really good at ai and they're gonna like not like they're not gonna like let the consumer you know market just disappear because it's actually an attractive business model as like there's nothing about having an ai answer from the google experience that would be bad from monetization and so like everybody that wrote google off three years ago was like it's very obvious to like like google wants to go do this one kind of you know fully conversely there's a lot of business models where like over the years we saw like there were a lot of incumbents that didn't wanna move infrastructure to the cloud because if they moved into the cloud instead of having like ten thousand customers they would only have like three or four customers and i was a totally different business model for certain software providers or certain infrastructure providers and so you could kinda see who is gonna be under pressure as the cloud grew so i just use these frameworks because they they kind of help you predict again like how is an incumbent gonna respond are they gonna respond in like a way that is is sort of like closed is is are they gonna respond with the right set of you know kind of mechanisms and that that just happens all the time ai you know at you generally is is you know kind of playing out with with not that different of response mechanisms from the incumbents that that you would also again kind of expect like who's who's gonna go and and kind of enter each market who's gonna how are they gonna compete etcetera are you only interested in that in this business strategy stuff like whenever i read like blue ocean strategy a lot of times i think dude this is for like a business that is this is like box this is like a you know multi billion dollar company who it can can swing up and become a tens of billions or hundreds of billions of dollar company over the next decade not as much like from a smb lens like for example where i live in new york city we have this thing called pop up bagels and like it's like i kind of an interesting take on a bagel like i think they've actually just raised vc but like instantly dis proving your question but like do you ever think about do you like nerd out on like you know we were talking about i forget the guy's named matt friedman who bought you know the baseball card company not turner not turner sorry do you ever of it from that perspective i do i definitely do nerd out but only if it like crosses my universe so i had a friend actually that had an online balloon website and he got he was selling kind of balloons to some wholesale some consumer and it that was really fun because because we could go in brainstorm like how would you do a consumer or wholesale kind of like party supplies business at scale and so yeah what i mean it's like i i i don't find myself being able to as much but like it is always fun to get your arms around we well we were always brainstorming me like how do you compete with party city like okay so like they've got this one complex thing because they have in you know physical infrastructure which means they have a high retail you know kind of cost so so it's hard for them to go as as full kinda of digital and and so there was a lot of like you know classic and incumbent in dilemma i think every every you know two person startups ups that are selling physical things in the real world run into the exact same you know market factors that that a a software business you know with vc run into if you were rewind the clock your your called student you know when you started box the internet enabled ideas like that if you were free young hungry to do something now what do you think you would wanna go build just because of of my tolerance for pain i would probably end up somewhere right in the in the center of the ai craziness just because i'd have to i'd have to give it a shot you're probably doing what we're all doing which is at like nine to ten pm you're like toy around on reddit or whatever and like look at all the nerdy cool stuff what what what is catching your eye in the last past couple weeks bribery nothing has changed sadly in the past couple weeks but my my stack is not surprising it's it's like like every tab is is one of or every ab icon is one of codex cursor per complexity cloud fig like i i have everything and i'm like like like per complexities like if you want like cloud based computer use that's gonna really go to the website and read each line of text like i i'll click off to per complexity computer if you you know if you're just doing basic research you have you know a number of options if you're building a prototype website you know i i play with you know a few different tools so not nothing surprising on that front what do you think about what going on with the public markets in terms of software because that's in that interests us right now like i think sean was was he had written down here what did you say sean do you think this is a generational buy i said yeah like you know permission to talk your book yeah either is is software right now in a in a generational buy spot or you know make the case yeah you you you can talk about it yourself or other companies well it's if i i'm very nervous about about any investment advice on this topic simply because you're at the mercy of many other factors of like is it you know chip trade week which just means software goes down no matter what and so like you know i i say i'll make you know separate investment advice because i don't know what the right kind of multiples are at any given moment for this stuff i would just say people probably for the first time ever started you know tweeting things like system of record you know nine months ago or whatever like and and but like but if you if you kinda take out any of the the temporary zeitgeist nature of any of that and you just like go back to the core of of like literally system of record software these systems are used as like the authoritative place where your accounting data goes or your you know your customer data goes or in our case your contracts and financial documents go so these are not the things that like are high on the list of i'm gonna go and just like try and build a totally alternative different system for and i wanna build it myself and i just want because i wanna go and you know save a few hundred thousand dollars or a million dollars like these systems are in the in the kinda of core guts of of these companies so that sort of is why a lot of the software that people say oh i vibe coded it in a week that that doesn't that doesn't necessarily equate too old than like like ford is gonna go and replace their erp system with that vibe coded thing like yes you were able to stand up a prototype that was functional but it's just just like totally different from like running your your you know enterprise that that is that held accountable to the sec and a global supply chain on on powering that so that's that's like why a lot of software won't go away in the same in the the same way people think but then the upside which is much more exciting is what happens when you agents that are running around and they need to go do all this useful work in your enterprise well the useful work they're gonna do is gonna require access the data that's inside these systems and it's gonna often require kinda guard rails that those eight that that that the agent is sort of participating and and ensuring that you know the agent just doesn't go off the rails and completely change out you know fundamental parts of your erp data or your crm data or you know kind of a core workflow so they need deter software that they are kind of participating in that have the you the right you know walls the right data access the right permissions the right workflow design that's largely gonna come from existing software simply because that's where the workflow have already been built out in those enterprises so there's a lot of actually ways to argue that there's more upside to certain software categories once agents can participate in those workflows because you can just do now way more with that software so in our case we actually see an increase in usage because agents are now roaming around accessing all of this data and you want them to access the same data that the user has access to which means you want something that has like reliable permissions and access controls and whatnot so that it really just becomes a question of like how do some of these incumbent software companies monetize that agent upside and and i think you're gonna see you know mostly it's mostly to be like a consumption oriented model it'll be on this more more of this headless approach but i think there's gonna be a a a ton of usage of software as a result of the agent you know kind of an adoption piece but again hard to then say like okay so what should you buy or sell based on that you have to everybody has to kinda go and do the work and and sorta of try and make a a judgment call of like what software will get used more because of agents which is what software gets used less in the in the future because of that yeah we were you know we work a lot with hubspot and we were friends with der and brian and and those guys it it's kind of insane the the market cap is like two and a half times the revenue and the revenue is growing thirty percent a year or something like that yeah it's crazy it's crazy crazy crazy i i i tend to believe it it will go up i just don't think that like a plumber missouri is gonna make their own crm yeah yeah i think the for good reason like we we tend to have a you know kind of a simplistic binary approach but like you look at vibe coding and you say well vibe coating must then replace the you know the the software that we already use and probably the real answer is no it'll probably just be built on top of the software that we already use and so it'll be the it person going and customize it their workflow even further but on a data stack that they trust is reliable and and and and you're gonna work you know very effectively it's kind of interesting the signal that you see it so in drop biggest announcement other than fable and like the past month is this thing called claude tag where you you work with a claude you know kind of colleague in a you know in a shared way well guess what system they launched in slack why do they do that because the users is are already in slack and slack has the right effectively permission boundaries to be able to have a a shared collaborative agent that you would work with and what the what why is cloud tags so powerful it's because it accesses your software systems that you can give it access to data so box is one of those data sources as an example so instead of it's sort of being like well cloud wins so saas loses you actually can be like oh no actually this is this intelligent substrate it offers some set of of kind of very useful use cases but then it's probably gonna also exist within deter software that also has a a bunch of use cases that that you know kinda create value so so i think once you kind of move on from the zero sum nature of like you know okay i'm gonna go prompt my way in the software every single day to no i'm going to like have some software that is always there that is reliable and deter and i'm gonna have intelligence kind of get added to that that does more non deter things that's probably like a more logical balance that you'd expect in the future to you're awesome you're smart a shit we'd love talking about i mean you only talk about the things that i know so if you i can give you lots of topics that i'm not prepared to right discuss this out enterprise ceo has take on enterprise like wow no so enterprise software dude thanks for coming on man we've we've enjoyed following you for a long time it's it's been fun and getting to hang out with you here for a little bit that's it that's the pod i feel like got rude where better know why i could be what i want to from at all in it like a day's off on a go less travel never looking back alright let's take a quick break to talk about a podcast because if you're listening to this you like podcast and what's better than one podcast another podcast and let me tell you another podcast you should check out it's called success story if you like hearing about different success stories and hearing q and a sessions with successful business leaders or hearing keynote presentations or just checking out conversations about sales and business and marketing tactics this is a great podcast for you so check it out wherever you get your podcast