I failed 22 times... then I built a $2.5B Company | Christina Cacioppo from Vanta

Date
Duration
50 min
and up time my email is christina at us dot com and it's like the right side at dot com it's way more powerful than the left side and now you're giving that up into what are you betting on the left side you're betting on the left side and like why would you do that and like what do you think will happen here i feel like i could rule where to i know i could be what i want to from at all in it like a days on on a road less travel never know fun fact do you know what you katy perry and serena williams have in common god nothing you're all on forbes self made women say butler and you are ahead of them is kind of amazing preferred that list never existed yeah so you have the midwest modest yes you're nothing good will come from that list yeah yeah those lists are who's there sort of made for the wrong type of people yes or jail time later so driver the while laugh that it was never under thirty under thirty i'm deeply glad about that battle yeah that turned out to be an anti signal you know what when i was thinking about this episode the way i think about it is like where you are today is where a lot of people wanna be you have a company that's working it's got like a cool startup up name it's again a cool office in san francisco the last valuation i believe two point four five billion but who's counting today you're at where a lot of people wanna be but if we rewind the tape to me when i looked at your story i think the through line for this is not counting yourself out so i'm a put that out there that might be true or might not be true but the the the basics of it is you you had a good job and you quit to try something new to try to make it on your own which a lot of people wanna but they don't take the leap you took the leap and it's not like it hit right away and you create advance and you created this you know multi billion dollar company right off the bat you did like thirty five things wrong or three five projects that went nowhere and i love that because i spent eight years of my life banging in my head against the wall with failure after failure after failure each time believing this is the time i you know let's start where you have a good job yeah you have the job at us usb which i think you kinda hustle your way into i was a stump stumble hustle okay didn't like stumble hustle they announced that job like they do all their jobs on the internet and said hey fill out this form if you want this jobs send into some links to your web presence and so i literally sent them three links oh to my web presence and didn't email anyone who knew them didn't you know turned out like new people from school who didn't pull anything just sent them links and put them in a form and was like well i'll go back to making slides what kind of links it was twitter flicker through the era of this and i had started design blog it a couple months before when i lived in berlin because i wanted to be like a designer who lives in berlin and those people seemed to have to design blog so i started one and that was it and they hired me and read something that was like the baby fred or somebody at the usb team was telling you you should specialize in crypto you should become a crypto vc is that true kind of was actually i was leaving so this was end of twenty twelve i had a lot of an because this job was great they were great you know like haven't you made it and i'm sort of like dude but i don't think like it and again what what's what's going on and one of my hang ups was you know what have i done why would anyone take my money right who's gonna take a check from me versus in my head of time matt ko this gpu no longer at benchmark but had this like ill silicon of valley career of like linkedin facebook benchmark you know on your like neither mac cola everyone will choose mac cola like a hundred of a hundred times which is let's say maybe a apart partially impostor syndrome but also maybe hyper yeah i'm been going yeah but like also true anyway i i basically said that they're fed me so two things which or you a couple things out deeply insightful one was like well yeah one christina you've gotta like get over that and you can either get over that bike sort of out hustling people and like kind of the fake till you make get strategy and you're sort like look i've seen in the office for two years i've worked with me you for two years it's like you're not you're not gonna be good so you probably shouldn't try that one the other strategy is pick something go deep in it and be the expert where no one else is and and in the fall of twenty twelve i recommend youtube's crypto really good advice on a bunch of dimensions right i didn't take it but like because you didn't make shut door you were just like that's not me and just like i don't know if i won't be an investor okay even though it's great and it's wonderful and all these great attributes and like everyone else wants to be a vc but like i wanna go make things so you decided to go make things take me back to that decision was that easy no i'm so interesting was everybody padding on the back and say you're gonna make this happen talking about what did what my plan was was i'd save my bonus from the prior year and it was gonna like a finances bonus and i was gonna live off of that as long as i could so like no job but a bunch of structure learn a code learn to make products hopefully something would come out of that and very much pitched as that it was not pitched as i am going to start a start up there was pitched am going to teach myself to code because that's how i saw it and thought about it and like yes i wanted to start a start up but i'd seen over the two year of so many people start startups to start them and then get into them and then be like i don't wanna work on this but now i have people in office investor like i can't stop but i think there was i think people took that conservatism as oh you shouldn't be doing this and so specifically there was a i mean there was a bunch of like why who no one leaves who has the option of staying why would you do that or don't you wanna work at some other venture firm or oh you wanna code why don't you go to grad school stanford has a great graduate programming computer science why don't you go work for somebody else because clearly you don't know what you wanna do and then some amount of like kind of the tougher stuff i think we're a cup one brief in particular it had been close to and who is very like just the left side on the right side of your email address and time my email is christina at dot com it's like the right side that dot com is way more powerful than the left side and now you're giving that up into what are you you're betting on the left side you're betting on the left side and like why would you do that and like what do you think will happen here so you have the good job yep you quit you hear the look you took the rights out of the email which was the powerful part you threw it away you're betting on the christina part of which there are men many and your plan is not even to go start a company to learn how to code and you're gonna teach yourself how to code by going on online and learning how to code that way and my understanding is that worked because i went to your website well you have this like list of projects perfect i built all these things yeah none of what you've heard of yeah not mostly went nowhere there's something romantic about that too i'm gonna go in a cave and i'm gonna yeah reinvent myself and learn this magic super superpower and i'm gonna train in the mountains where nobody's looking and i'm gonna come back stronger yep it may not have felt that way at the time but but like i kinda knew it was supposed to feel that way and then day to day there was some men of like i spent more than my like daily cash flow i know but like i kinda knew that what i a better version of me would feel but practically i knew i was a person who benefits from structure and it's always great doing for myself so what i did was a friend of mine had just sold a company to ebay new york and opened up this eve this big space in new york that was actually right across the street in the office and so i got up every day and i got for my job and i basically walked to the same place but i went in a different door and then i sat with those engineers and they address up by the way because i i feel like there's psychologically so totally to actually dressing it like you're going some i dress but it was like did not wear a from right like yeah yeah and then i go and i'd you know show in the morning and i'd like do my audacity tutorial or try to understand general javascript to to varying degrees and then like go home at you know six pm or seven pm and then often like you doing stuff but basically it was like tricking myself and into acting like i had a job so that i got up every day i was there by nine but you know i was just doing the thing and i and i do remember there was a time my family took a vacation that i went along with in january and i came back to tan and i'm when was like where were you last week like basically like why weren't you at work why are you ten and i was being like i'll pay for this to like i want chalk i'm everything is pto to me but it was like also a like oh yeah i got this like that's that was kind of like a fun fun moment too yeah like that so you have this era which is kinda like in the movies it's the montage it's they just fast forward through this part takes two minutes even though in real life it's two years and you have this thing written right on your site that i love this quote and i think in my research this was my favorite thing i pulled for you which was at the top of your site it says the function of the overwhelming majority of your artwork is simply to teach you how to make the small fraction of your artwork that source and this is from a book called the art of fear can you i love that can you can you explain that yeah i i that's deeply drove creative projects and i think start sort businesses or you know internet art is like they're all creative projects one thing i learned at us seeing seeing people bitch but then like hearing the stories behind their big you know tumblr twitter fours square whatever all the big successes of the era where when i walked to the i was like everyone is mark zuckerberg not actually but like everyone you know like start founder or people who have an idea visionary and they go into their room and they build it and everyone uses and it's like the first or second thing they've done and like facebook speaker but con all of mark's projects and so like that's the way you know i'm like i'm like shoot i'm like not never worked for me so i'm i'm probably not one of them and you he was just so helpful in abusing that notion and being like look some people like a very small number of people can do that and that's incredible i wish i wear them i'm not most people actually try a bunch of stuff and eventually something might work but it's like at best thing five and it might be thing fifty five but no one really talks about that because it's both because it's like painful and kind of not fun you know it's supposed to be romantic but actually just kinda sucked to hungry for two years literally and and metaphorically and it's so much nicer like you get so much of praise for sort of being like the brilliant person right and that's the expectation too i think i just had a like oh yeah but like that's just encouraging so many people from starting it's sorta like when you write a bunch of movies about love and then you're like this is what it's like yeah i will bump into a stranger are papers off fall on the floor who'll help a people swap a paper he'll have to come find you because i'm not into him but he just pursues me anyway then it's like if you have that notion that that's how it goes yeah you'll almost count yourself out of other things that could have worked otherwise it's like that you know if watch the social network you're like that's just how it is brilliant genius has has a vision does it takes off and then he rides that bull yeah they're at the rodeo we actually after i read this quote on my team we started using this phrase just called bad art mh so i'll hit up my team in the i hey let's make some bad art like intentionally just almost lower the stakes instead of we have to find the next big winner idea right let's just make some bad art today yeah and the analogy i gave us said imagine like you know you go to a hotel or a hotel you're doing something you're go to a place that you've never been before maybe nobody's been there before when you turn on the tap like it's muddy water at the beginning yep if you look at that and your it's like you're mortified by it it's disgusting you'd turn it off right away and like you bad right leaf but if you know that actually that's the process sort of have this muddy water of bad ideas and bad scales at the beginning and get it out of your system then suddenly the water starts running clean and i think that framework is is just very useful for anyone who's doing either creative endeavors or startups which are a pretty creative endeavor too do you know the story about making pots no from the same book so and i think it was like around the chapter where that quote was but anyway was an art teacher and he said okay art school pottery class you have one assignment all semester you have five weeks to make the perfect pot you can turn in as many pots as you want but i will judge them all and the highest grade will go to the person who as the best pot and student one spends all semester crafting the perfect pot and handed it in at the end and student two makes two pots a day and they're all back for a long time right but over the course of the semester hands in whatever like three hundred pots i'm like who gets a better grade of course the three hundred three hundred right yeah but it's like that concept yeah it's like so we have to live it almost yeah so that's to really internalize it yeah actually a great thing i did once with my company there's you've probably seen like the marshmallow test like the site test with kids it makes a good point which is you give a bunch of supplies to you break your team into a bunch of groups groups of maybe four or five and they get like sticks of spaghetti one marshmallow and there's something like maybe a string and like two other things like a piece of tape and so the idea is hey you have an hour at the end of the hour i will come around i will measure whoever from the tabletop has the highest marshmallow so whoever could build the biggest tower once and what most people do what my team did and everybody who does this the first time pretty much is you immediately go into like the way we do most things in corporate life so it's kinda like okay you're in charge you do that you sort of segregation of duties you start trying to like plan and then you so you sketch a little bit then you start building the tower and at the very end like okay okay what's almost time put the marshmallow on and the entire thing collapses because even though marshall looks so small in like light yep compared to spaghetti sticks it's way too heavy and you don't realize that because you didn't like you like back loaded the possible failure you know the the failure mode or or the sort of test of the of the idea you spend all your time kind of planning and architect this brilliant beautiful thing and the the cool thing that they've shown in this is that when they do it with kids versus adults the kids right away either eat the marshmallow or put the marshmallow on right away and they're like oh it's too heavy you have to have like five spaghetti that hold this thing up they figure that out right away they don't kinda save that to the end to try to perfect it yep and that sort of iterative thing about testing the risk assumption yep is is maybe important it seems like for you did you make that mistake of kind of like over analyzing over planning at the beginning but like not testing with customers less the very beginning because at the beginning i was just bill i built a book website it was like good reads but better but it was actually worse because i didn't notice doing that and but like it was something for me this confused everyone else right because they'd be like well you're well not you know what are you doing without having a job and i'm like building a book website and then they'd be like are you gonna compete with amazon no like are you gonna compete with good eats and you're like well you know with my with my friends but like no you know and then they'd be like what would you say you're doing you know and you're like mostly battling javascript cares trying and like spend last time on stack overflow you know being anyways this is a cold confusing thing but the beginning it was just i like like when i would go visit a friend's apartment i'd always like be drawn to their books bookstore if you wanna see it's on their books show anyway so was like okay what if i can get everybody's these books online but it was like clearly this is not a business right like best case i'm making like fifty bucks a month you don't amazon referral fees you like not a business but you did it anyways why because i wanted it i want and it was a good it wasn't you know like you do your initial coding tutorials and you like or making whatever the other person wants to make which is not what you wanna make and like i actually wanted this thing and it like forced me to be like oh you know now i want like in animation when you shove the book so you you're right and then you'd like learn about css animations whatever it is and so you so you start building stuff for yourself yep did you ever switch gears to okay now now i'm gonna do the startup up startup i'm gonna do the thing that might actually yeah you know get me out of poverty like self induced poverty basically so at that point i was very like look you know just taught myself out to code and like you know am i that good no but learning how to do some of this it's much harder than it should be and a lot of it's because their programming tools make us like hold everything in our heads and you have to teach yourself to think like a computer and like read their code just like not how a person you know we think like a computer and when do you have that everything gets easier but like why we are typing on computers and so i kind of got on this like if we can make our programming environments better you can like more they will just make more sense and more people will like learn to code and so you know i was willing into that personal problem also the like you know live in the future and build back you know whatever all that all the startup up trope advice i'm curious about that what startup up t advice actually helped you i think the build something you want is a bit of a red herring it works in some cases but you're also very limited to your experience it's kind of like when they tell writers right what you know and then you like you know it's like a fourteen year old who's had charmed life and like they just don't know that much and so like what i gonna write about and so my version of that is like look if there is something personally meaningful like by all means go for it that's top ranked totally but like second best is like find someone else with the problem and deeply deeply understand them i think there's a avert the shut your eyes imagine the future what it look like build that i this makes sense in retrospect i think in the moment it's pretty hard to generate reasonable startup up ideas during that right but again i can tell you a story about van that where van fit that yeah it does but it's but that's in retrospect yeah so what was the actual in the moment way that you stumbled into this idea of that now seems obvious as all great ideas do once once they exist now there's you guys and some competitors trying to do the same thing but that was kind of a novel idea and it was a new part of the market at least yep what was the insight for that the insight was wanted to start a security company that started serving startups there seemed to be like security was this huge market but no one is really focused on startups ups and start to new security tools and was of like why and like when does this become a ninety point billion but like go from a zero tam to like ninety quad trillion dollar market science in precise rooms yeah that's the official number exactly but wait why security because like you know when i'm talking i've been talking to you for i don't know twenty minutes now you don't strike me as somebody who's wake up every morning and i was thinking about security during that year off what why did you even think about security to be begin it seemed really interesting it seemed like this kind of competitive cat and mouse thing where they with attackers where there's like kind of a real board right i think one of the things i've i've i guess i but i didn't really know like i'm very competitive should have played more sports as a kid didn't through van to have an outlet for a lot of that energy which is great i think honestly when i was at dropbox they worked with this product security team and they were great they were super fun and they were really good educators and i not like they hosted you know seminars on things it's just like they wanted you to fix something they'd come over to sit next to year and explain why it was important and how and all the anyway they were just great and so incoming with startup ideas there was a bit of like well this actually seems like a deep enough interesting enough space that if i work on it for years so there'll be lots of things and if i can't come up with anything and end up burning you know eighteen months of my life learning about security on the internet good a been worse yeah really you kinda look back and be like okay worst case nothing comes out of this but like i you know i'll feel as good as i will adopt me so you you took the year or multiple years off to teach yourself two years yeah but then you go to dropbox yeah so you go back to getting a job yeah so i feel like we like there's a part of the story that's like i iterate reiterated reiterated it finally found it no no finally you found a job at dropbox yeah because i was kinda like okay now i can code but i've never had a real job i've never worked at a company never worked with people also my my like friends are kinda getting promoted and like i can yeah like unclear from employ like this seems bad and i was really frustrated because again they're like i wouldn't tell people i wanted to start up to come out of that but like i did but i also at the time was like well nothing i worked on should be a i start up right so what what was that story you told yourself so you you spent the two years you bet on yourself yep which sounds amazing that's a great t shirt bet on yourself yeah but the reality of it i do it for i told i do for eight years yeah and i was delusional enough to keep going yeah but also objectively it was bad and i should've have i had to tell myself certain stories in order to either keep going or to like just maintain a self of a sense of confidence yeah beyond that because the evidence was telling me you suck yeah yeah and i just couldn't tell myself you suck because then i definitely suck yeah what were you saying when the evidence kinda said you suck this is very silly i had this like survey i would fill out a google form i'd fill out for myself every sunday or every weekend what are you working on how do you feel about it what do you gonna like what's your next goal what do you did move forward you made that for yourself me it for myself it was like a personal accountability thing right okay and i asked a bunch of questions they were all useless the only question that ended matter was what would make you stop working on what you're working on right now and to your point turns out my present self always thinks i should keep going but my past sometimes thinks current itself should stop right so was actually like looking at those answers and being like two months ago i should said i should stop if i got to the the point i meant now i don't actually think i have counter reeling evidence i just had stubborn this shoot i should probably stop and so that's how you were stopping those projects yeah you when when we i sent you some questions ahead of this to try to understand what what you think is important to talk about what do you think is insightful you said something that i really resonate with which is managing your own mind managing your own psychology is one of the most important things yeah how does one wanna do that and what's like how would you teach that to somebody else or how would you talk about that to somebody else it's i think hard hard to do hard to teach i think what i try to tell people is figure out what like it's it's personal and not personal sensitive but like personal like specific to you and figure out what makes you happy or centered whatever those things are and like do not give them and so for me for years there's was like a you know running three or four times a week and like exercise sure but it actually just like the mind clearing cath kind of medi like running and you know it's like running for me but like whatever for someone else and it's like whatever that thing is do not give it up and i don't care how busy you get but sort of know what makes you feel like you and don't drop those things know what things make you feel like you which is kind of like you what you're talking about is habits and hobbies is that more of what you're can it's like that feeling where you're like you're you're like move through the world and you like feel like you're at your best you know like you're the best shin version of yourself it's like what brings that on so for you running is one what was one reading like not in any i mean kind of an elegant the unlocked show but actually just because it is something i have done since i was six years old right and so like if i think of hobby either there anything i've been done through my life reading it was actually one of the biggest through line right and so there's a part of that that just feels like me yeah because i was looking you read like i don't know like thirty fifty books a year or something yeah but it's it's like any of one of other things and like blah but actually just like it is centering i feel do that when i was running a company and and by the way my mine was not a two point four five billion dollar company i was like i have no time to are you kidding me there's problems everywhere i'm drowning your problems and did you just replace tv with reading or something i was that yeah like actually eric told me that you are like extremely quick with reading he's like she would take a bus to work yeah and read the bus and read the whole book yeah on the bus ride oh yeah i mean over the course of a week or so but yeah like actually tuesday the way he said it take more legendary he was like now to and from cover to cover no oh got it i should usually actually still take a bus to work part of it so i can just sit there and like you bus to work yeah because look if i take a car i'm just gonna like sit in the back with my laptop writing emails you know and in a bus like i want san francisco boss i'm pulling on my laptop on that well something like really gone wrong and so it just forces me to like sit there and have twenty minutes between home and work and i like it's almost like small you know people are like obsessed with cold plunge yes i think the more hardcore version is take us san francisco so close to work it's like oh you can endure a eighteen minute bus ride but like that's for the losses aren't bad five hour used to be my boss five hours like i used to take thirty eight and thirty eight is like a actual zoom any happened yeah yeah no five are great bus i miss it i mess okay so so benjamin your psychology said figure out what makes you feel like you most of you and make sure you stick with those things keep doing those things it'll kinda keep you you centered with it what about then your own psychology when it comes to self doubt when it comes to getting down on yourself because i spent two years i didn't really land where i wanted to land with it did you have a conversation with yourself there or a store you told yourself in order to to yeah i was so annoyed i was which is retrospect i was like being so pre just like life was good you know again like the the bad like my worst case outcome was becoming a product manager a dropbox light of dropbox is power like my life was great could you just say the bat yeah great really like my life is great it did not feel great at time it was totally great and again i knew i was like five percent aware of that ten percent but that's not the lived feeling do you use negotiation terms like that just regularly hopefully fully not that sounds kind of obnoxious i'll try out too now no i like that and i've always felt that if you build a great silicon valley cup internally your company should be a totally normal person but outside you should have that like ten percent crazy yeah it just gives you like actually like two x evaluation it's just creates this extra horror it's true wow she's i she's should barefoot foot all the time blind oh interesting must be one of those real outlier types like oh my gosh alright i when i to put this list of ideas that you did so i've looked back in my career and even when i went through eras where i tried something and it didn't work a lot of the times i looked back with the benefit of hindsight now and i think oh i was just sort of an idiot about it i actually either stuck with it or done it differently or pivoted the market that actually was a good idea i'm curious do you feel that way about any other projects you worked on oh like there art projects and i say that with deep love but like they're not business okay the voice assistant for biologists yeah that doesn't sound like a great that was just comic bad no yeah there's like a deep lack of any commercials in nearly everything on that list which i think is part of why van has had commercials like baked in from the very beginning because i'd made that mistake learned so many times what about now so if you if you weren't doing this or in general like when you operate a business you see a bunch of pain points blind spots maybe like parts of the market that are una unattractive if somebody listening to this right now and they are looking for you know inspiration or ideas that you know spark thoughts in their head about stuff that they could go do where would you look what would you recommend people think about what problems do you think need solving but yeah i think so so much of what i think about that's not kind of directly in ban wheelhouse is something around like running a b2b b saas or being in a b2b saas business for forget running at just being in it there's like so like someone please fix the go to market tooling stack there's nine thousand tools and none and it's like you jerry to them together in this rub goldberg machine and the marble roll on the floor and like if anyone want be b sas just like fix that go full stack on all that but for people who don't want baby sas which they're are hopefully many i think the cross van came out of i mean of course like i mean i like to go in but of course i really like it but that was pick something you want to learn about and just go talk to anyone you can about like what their days are like what their problems are like just like what's going on and kind of try to develop a mental model in this space the story i heard about van which sometimes we bake up these respect stories so i don't know you you can i tried to actually tell that the true one like blink twice if it's true and yeah but it was you're at dropbox you work on this thing called paper which was remember like seen paper at the time it was like this idea of this like collaboration tool if you go to google docs yeah dropbox is google docs you go to launch it and it's like hey we don't have soc too so can't really launch or customers can't use it and you were like suck what yep and you didn't know really what that was and you were like so how do we get that and you started asking questions to try to understand like what is this thing that blocked us here if it blocked us maybe it blocks other people yep dropbox had a security team that was gonna be able to try to solve those problems but like the average startup doesn't yep and the next part of the story that i liked was even though you had just spent two years learning to code and built thirty five projects and code them up and shipped them out there or whatever you didn't write code for this you were like i'm gonna test this idea with an excel spreadsheet only yep and you went to one or two starters i think yc startups that you thought might need this and you were like hey if i did this for you would that be valuable and they're like oh yeah sure can you how much of that is true all drew the s part is all the dropbox have happened there was no light bulb i was like not smart enough to fill bulb over my head at the end wish so but it was just like learned about the whole process learned what it would take and then like basically ran screaming from the room they just sounded awful especially when trying to launch and even figure out if we had product market fit to the idea of like we're gonna go two years of work to then see if we product market fit you're like bad bad like how do find reality faster came back to it later did the stretchy spreadsheet thing and i think honestly it's like because it sort of five things on the list like kind at the point where you're like okay i can write you know maybe someone s jobs but like i can code the thing or code a first version of the thing that's not the hard part the hard part is does anyone want my thing at the end and so like how much of the validation can you front load there so i i think a lot of people hear that and they're like either they hear you should talk to customers you should people want this make something people want yeah i don't think anyone has any idea how to actually do it so what is the quick and dirty recipe for how you actually go who do you talk to yeah what do we really ask them how do you make sure you're not getting these false positives just by being like eager beaver and they're like yeah that would be a maybe i'd be interested and you're like they totally loved it yeah so on the false positives anything that is not can you do this for me now tomorrow next week is a no and people are really kind and they wanna be kind and so they don't say like rarely do they say no but a lot of like oh maybe next quarter or like i don't need this but my friend my oh hard knows yeah you should take my friend knows totally hard knows i think on who to talk to i mean we started like anyone who would talk to us and then it it was just like and that sort ended up being coworkers former coworkers because you had like some like i don't know you know anything about this topic but you're kinda of a nicest person and so i'll like give you a half an hour sort of thing and then just fan out from there at the end when they're like well i don't ask them do you have anybody else and they were list people and like say yes follow with customized like it forward you know like make it easy fee for them and just keep going out yeah i think that's an important one make it easy for them yes to do the thing they said they wanna do oh yeah like follow ups and be like thanks so much for meeting me like i would love to talk to your friend who eric who said this like here's what i'm working on like and just like soon they will like write them in email they will forward exactly yeah so you have you ever read this thing called the mom test yes do you subscribe to that yeah generally yeah the that was helpful to me when it was there's i don't even actually remember what was in the book only one line which was they can't tell you about the solution but they can tell you about the problems so all your questions need to be first about their problem mh and then at the end if you wanna ask them about this about your solution great but just assume they don't really know the what the solution needs to look yeah i think it's true try to avoid yes no questions just harder than it sounds and there's a bunch of kind of user research tips tricks of like if somebody must mispronounce to something go with their pronunciation but otherwise they're gonna don't break before exactly exactly like i think i do that and it yeah sort of is like a problem because it's kind of a know it all move right and then it makes them feel like their mind goes over there exactly am i i being stupid say something stupid exactly where you just like want them to like stream of consciousness that you basically yeah exactly do you have any good hustle stories for how van kinda got the flywheel going because you know startups don't kind of like like explode right away necessarily yeah and i've seen your like arr chart which looks like a beautiful high totally but if you zoom in and it's like wow that was a year where it's like pretty kind small and then then it started to accelerate was there anything you did that you felt was interesting unique that kind of to it's so funny looking back because like i sent a bunch of outbound emails to yc companies but i didn't know the word outbound at the time right i was like emailing yc founder her for feedback and i legitimately did want their feedback kind of to this but it was like half a like okay i'm gonna spend you know sixty seventy percent of the call talking about the problem and how you're solving in and then the end be like i'm am building a thing would you like to hear about it but it was like totally cold outbound you know i just like didn't know that word so you mailed a bunch of yc people that got the ball rolling what happened after that honestly the early strategy was like just do and try everything and then see what works so what did work the outbound worked there was a word of math we tried to actually really hard in the early days to basically build this call response in like founder or slack channels or vc slack channels where someone said talk to and someone else would say ban and just wanted this you know how do you do do advantage you're saying like build the brand in people's minds yeah and that was great for a while and then a bunch of knock ups came and there's a bunch of other ways to get talk to you and so that that association remember you billboard like what is a compliance at the too much yeah still up that was good still out yeah i joke with people like we make software but like we also make a billboard and we're equally known for both like it's like equally as as important what else podcast advertising really worked in i mean actually it still really works but like really worked in the early days i thought podcast advertising we're just gonna be like sending one out the window i was totally wrong and that's what happened somebody on your team pictures through this eric eric was like i want almost twenty k go on t this weekend startups ups or something and i like rolled my eyes and to find whatever go you totally where she was totally right eric is like this mythical totally leader to be now where i've only ever heard great eric stories and so i don't wanna hear if anybody has a bad eric story or an idea you had that did truth don't tell me please no alright i wanna ask you about to set a couple other of your controversial or maybe just less consensus opinions i've seen you write these somewhere on the internet you tell me if you still believe these and and why consistency is overrated this on your website oh yeah people read a lot into this i'm just like joking with myself because i say contact me through these four ways that are all of totally different names on them oh like it's is like my just yeah it's just like minor self awareness thing that i think people think is meant to be a broad philosophical statement do i actually think at the broad fill philosophical growth statement no probably not i think vance taught me consistency is actually underrated yeah second strike somebody who's consistency first yeah it's bad it's bad when the goal post move i don't know if you're saying you think this or that other people people to the advice tend to be right like you know if you're goal posts keep moving it's hard to have find happiness and like you're always something mean like what what does that even mean moving like i think i mean gets gotten lots of forms of life but like let's take startup founders just because right it's like you wanna start a company you wanna hire some people you wanna raise a seed round you wanna get to like a million in arr but then by the time you get there like actually i wanna get to ten right like yeah yeah that and there's like always something you are chasing and i think that it's generally seen as a recipe for unhappiness right like why can't you be happy in the moment you did this thing prior you thought was great like why can't you think it's great and i think i could be true in some cases but i actually think or i think the the the trick is slash downside is if you're like only happy when you hit a goal post and then you're moving them like you'll will never be happy she actually just like the work right it doesn't the matter and it's know a lot of things are more sustainable when you like the work especially when you have a lot of work to do my formula is progress equals happiness which is that no matter where you are sort of like the the y intercept doesn't matter the slope matters and so wherever you're at if you don't feel a sense of progress in your life you will feel unhappy and then you'll feel even worse you'll feel guilty for feeling unhappy yeah because you're like i guess i do have all these good things in my life but i still don't feel this way i'm just fundamentally broken inside i'll never be at right right when actuality it's just a sense of progress i even better progress a sense of progress in a direction that you have set out intentionally that you care about yep and i think that in that sense moving the goal post is great because you're saying i would like to continue making progress i enjoy progress so much i why would i stop my progress that stops my happiness a different way of looking at do you remember deep cut ten twelve years ago jess who that founder of poly four at the time now so corey wrote a blog post about founder psychology no what what did it say it was like what basically like wire founders always unhappy and she's like especially when their companies go like this and it was a line up into the right and she's like because if you zoom your again y access getting higher like what is this you know because if you zoom in on the graph it doesn't look like a you know forty five degree angle it looks like a roller coaster that is going slightly higher right right but it's like the roller coaster along the way and like you know again even when you zoom out and you've got this lovely forty five degree line the downs hurt gregory time yeah it's the peak to trough that you feel you don't really even recognize that you've gotten higher aggressively at this time you also have another one which is high high standards are bad you think that in general you so people don't say this but they imply it in different ways that you don't have such high standards right what is what what's a situation where that's come up for you or you felt that i think a lot of van stuff and i think within the company and then with you know kind of partners are folks outside and i mean some of the feedback we get that like i kind of i don't appreciate more than anything else is like people care people respond super quickly like you know we're getting something might have gone wrong but the person tri really hard to fit it right and i think those things definitely don't happen everywhere by accident it's not like i had i mean probably hopefully a smaller role in it but i think when people join there's a little bit of like oh the bar is here at atlanta like kind of scary did i join the right place like what's going on what's an example of where where would somebody feel that couple places but i guess in go to market are expectation they're on quota around attainment on that they're way off industry they're way higher and i think if you just if one just hear some them in a vacuum they're sort of like what is what like why would i why would i sign up for that then they join and it's like oaks you're surrounded by people who are like into what they do getting better every day wanna get better every everyday care a lot and that sort of environment can be like really infectious i'm curious did you ever read this leaked production document for mister beast were take a look at that do you see that going around like a few weeks ago i know do you know what i'm yeah so like right around the same time that program put founder mode out there in founder mode like wait what is it exactly in like i was like a yes what about what part of a lawsuit mister beast like the internal doc he wrote for his production team leaked a big part like we've gotten to know him and become you know pretty friendly with with jimmy over time and it's just done like the the number one thing you go hang out with jimmy for a couple days like you walk away and you're like oh he that's what people that's what it means when people say real reality you know steve jobs just to have this reality distortion field yep and it's and literally he he his company is based in like a tiny town in north carolina so like he gets people to move there and then once you're there you're in his bubble and in his bubble the expectations of what work is about what success is about what we're able to do about the timelines we do them on about what it means when something says no not possible and he's like one of his things they push past the no he's like you know you have to be able to push past the no you don't always have to get it to be a yes but like if you just come back and you said oh we you know we asked for the permit and they said it's gonna take six months and he like that can't be the end of the story and that we saw it on every little thing like for example we wanted to play basketball the next day it was midnight and somebody was like oh man i can't wait till tomorrow like i just wanna play and he goes well why didn't have to wait like we'll midnight jimmy what he can do he's like i'm sure there's a gym around here somewhere let's go let's go find one and we're yeah but they're gonna be locked midnight like schools aren't gonna be open he's said call the athletic director he's said say just call call all of them right now in the county he will take us twenty minutes and offer any of them a thousand bucks see have to come open and like part of it was like oh just throws money at every problem but actually it's not about throwing right money at it it's yeah everybody else would immediately just default to like is not possible not feasible not not gonna be doable whereas his default assumption on any any given thing is like why not of we could do that yep it's just a matter of deciding if we wanted it we'll do it if we don't we won't but that's it and then you just see that time after time after time hanging out with them on big things like you know the videos that they're gonna go shoot but the small things and it's just a different year gear it's like oh your gear is like my my stick shift only goes to six yours just goes to nine right i'm gonna hang out with you i now need to decide like how i'm gonna get to eight or nine because otherwise i'll just be sticking out it this won't be the right place for yeah it totally and i think there's i mean i think also if you like experience that and you're like you know what i'm go with six right totally reasonable with the decision like not that you know arguably you maybe be a better decision in some case it's like totally fine but the so like there might be there might be a nine for any given thing i think it's a helpful mindset you also raised a bunch of money late so you didn't raise early on you got to ten million and arr before you went and raised your series a yeah i'm not so curious about as to why you did that because i'm guessing the answer is pretty simple which is like we didn't necessarily need it we just stayed focused on selling the product that was working but more so when you went to go do it what was that experience like because oh it's you're yeah it's great it was really funny so people or vcs in san francisco broadly like knew we were doing well because of kind of the slack channel chatter or like van had come up they sorta didn't know how well and so there was one pitch meeting i remember where they and sorry you kept it closely right now look on purpose because basically where were like we have this great idea and everyone else thinks the candidate wouldn't like spell what we're working on think it you know has k's and to doing things in your feet and i would rather they not know because then somebody's gonna start knocking soft and copying but anyway very smart vc very good at his job like go in pitch and i start working through the slides and i get to the era ramp chart but you know ten at the end of basically and his jaw dropped and he was like clearly speechless and he's looking at it and he's like i that you were at like two and a half and you're like oh that was you know the they i know ten anyway i was like keep growing i at the end of sort of like we're like not gonna like we missed it like we're not gonna be able to do this i can like try to introduce you to someone else but like you know it was fine like fine like you know there were other people but it was this kind of interesting pitch experience and then basically i go into meeting with another vc was he's very good at his job and he's like you know what thought you at nine point four because i'd like taking your twitter chart and backed it out i did the same actually i one the pixels don't know i put proportions it was like she said ten so if this is ten yeah where was she a year ago yeah two point seven or whatever he had basically done that and that was also here you're like was great it's so good at your job it's so fun is that you end up going with or no no you're great what's greatest calling yeah but i think actually it was till the goal post stuff and i'm you know i'm not very good at tele breeding but it was a moment where i like took i mean it'll i'll beep like a week i was like no i am looking at tell this story and what we've done and like i'm deeply proud of it and i wanna told you that but now i like feel overwhelmingly proud of it right and like here's how the pizza fit together here's how will fit together and i believe it so that was just then became like i still kind of hate fundraising but it was talking about something i believed it just fun right right eric told me that he thinks you're great at negotiating you said funny you said that's surprising to continues but he he was not he was not wishy washy about yeah he's like she's incredible at negotiating one of the best i ever been around asking how or why she does it so no pressure what no it's you're really surprising i think if i'm confident i'm actually confident in it and then we'll just stand and like not blank not sw if we're playing chicken we'll eat the marshmallow it's like i got it like let me know when you want these terms i'm happy to sit here and wait and actually truly i'm like happy to there and wait at that point so i think it's just a lot of that it's like i won't i believe it i won't flinch cool well thank you for doing this this has been amazing should people you find you find van maybe you give it a shout yeah vantage dot com v a n t a dot com if you need any help with anything security or compliance related who would love to help you something thank you for this thank you so much i feel like i could rule to world i know i could be what i want to put at all in it like a days off on a goal travel never looking back

Episode Notes

Episode 646: Shaan Puri ( https://x.com/ShaanVP ) talks to Vanta founder Christina Cacioppo ( https://x.com/christinacaci ) about quitting her job and betting on herself. 

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Show Notes: 

(0:00) Stumblehustling into USV 

(4:36) Betting on the left side of your email address

(8:30) The art of fear

(11:47) Making bad art

(13:30) The marshmallow test

(17:26) Startup advice to beware of

(18:16) The idea for Vanta

(21:00) The only question that matters

(22:30) Managing your mind

(27:47) How to pick an idea to chase

(29:03) The real origin of Vanta

(31:00) Building a flywheel

(36:06) Controversial opinions

(40:49) Pushing past the no

(46:17) Not flinching during negotiations



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Links:

• Vanta - https://www.vanta.com/


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Check Out Shaan's Stuff:

Need to hire? You should use the same service Shaan uses to hire developers, designers, & Virtual Assistants → it’s called Shepherd (tell ‘em Shaan sent you): https://bit.ly/SupportShepherd


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Check Out Sam's Stuff:

• Hampton - https://www.joinhampton.com/

• Ideation Bootcamp - https://www.ideationbootcamp.co/

• Copy That - https://copythat.com

• Hampton Wealth Survey - https://joinhampton.com/wealth

• Sam’s List - http://samslist.co/


My First Million is a HubSpot Original Podcast // Brought to you by The HubSpot Podcast Network // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano

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