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

And time my email is Christina at USV.com. And it's like the right side, that USV.com is way more powerful than the left side. And now you're giving that up until 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 can rule the world, I know I can be what I want to I'm putting my law in it like no day song on the road, let's travel never. Um do you know what you

Katie Perry and Sarinda Williams have in common? A good nothing. You're all on Forbes self made women list. And you are ahead of them. Yes. You have that Midwest modesty. Yes. Those lists are um They're sort of made for the wrong type of people. Yes. Um Or jail time later or something. I was never on thirty under thirty, and I'm deeply glad about that now. Yeah, that turned out to be an anti signal. You know, when I was

Thinking about this episode. Uh the way I think about it is like where you are today is where a lot of people want to be. You have a company that's working, it's got like a cool startup name, it's a cool office in San Francisco. Last valuation, I believe. Two point four five billion, but who's counting? Today you're at where a lot of people want to 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 gonna put that out there. That might be true or might not be true, but the the the 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 do, but they don't take the leap. You took the leap. And it's not like it hit right away and you create Vanta and you created this, you know, multi billion dollar company right off the bat. You did like thirty five things wrong. Uh or thirty five projects that went nowhere.

And I love that because I spent eight years of my life banging 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. Um, you have the job at USV.

Which I think you kinda hustled your way into. I was saying stum stumble hustled. Okay. They announce that job. Like they do other jobs on the internet. And said Hey, fill out this form if you want this job. Send us 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 I like knew people from school who knew didn't didn't pull anything, just sent them links and put them in a form and was like, Well now I'll go back to making slides. What kind of links?

It was Twitter. Clicker. Through the era of this. And I had started a design blog.

it a couple months before and I lived in Berlin'cause I wanted to be like a designer who lives in Berlin and those people seem to have design blogs, so I started one. That was it. And they hired me. Which is crazy. And I read something that was like they

Maybe Fred or somebody at the US V team was telling you you should Specializing crypto. You should become a crypto V C. Is that true? Kind of. It was actually when I was leaving. So this was end of twenty twelve. I had a lot of angst'cause his job was great. They were great. Yeah, like Haven't you made it? And I'm sort of like, Ugh but I don't think I like it. And again.

Wha what's what's going on? And One of my hang ups was Uh 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 at the time, Matt Kohler. This

uh GP was no longer at benchmark, but had this like illustrious Silicon Valley career of like LinkedIn, Facebook Benchmark. You know when you're like me versus Matt Collar, everyone will choose Matt Kohler like a hundred out of a hundred times. Which is let's say maybe a part partially imposter syndrome, but also maybe hyperlogical. I think like yeah, but like also true. Anyway, and I I basically said that to Fred, and he said two things which or he said a couple of things I would uh Deeply insightful. One was like well Yeah, one Christina, you've got to like get over that. And you can either get over that by sort of out hustling people and like kind of the fake it till you make it strategy.

You're sort of like look. I've seen you in the office for two years. I've worked with you for two years. 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 in the fall of twenty twelve, I recommend you choose crypto. Mm.

Really good advice on a bunch of dimensions. Right. I didn't take it, but like Because you didn't believe in crypto or you were just like that's not me? I'm just like, I don't know if I want to 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 V C, but like I wanna go make things.

So you decided to go make things. Take me back to that decision. Was that easy? No. Was everybody patting on the back and saying you're gonna make this happen? Definitely not. What I did, what my plan was was I'd save my bonus from the prior year and of kind of like a finance bonus. And I was gonna live off of that as long as I could. So like no job, but a bunch of structure. learn to 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 startup. It was pitched as I am going to teach myself to code.

'Cause that's how I saw it and thought about it. And like, yes, I wanted to start a startup, but I'd seen over the two years at USP, so many people start startups to start them and then get into them and then be like I don't want to work on this, but now I have people in office investor like I can't stop. But I think there was

Uh, I think people took that. conservatism as Oh, you shouldn't be doing this. And so specifically there was a l I mean, there was a bunch of like why no one leaves US V who has the option of staying. Why would you do that? Or

Don't you want to work at some other venture firm or oh, you want to code, why don't you go to grad school? Stanford has a great graduate program in computer science. Why don't you go work for somebody else?'Cause clearly you you don't know what you want to do. And then some amount of Like kind of the tougher stuff, I think where a coup one person in particular it had been close to and who was very like

Just the left side and the right side of your email address? And the time my email was Christina at USV.com. And it's like the right side, that USV.com is way more powerful than the left side. And now you're giving that up until 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? So you have the good job. Yep. You quit. You hear the

Look, you took the right side of the email, which was the powerful part. You threw it away. You're betting on the Christina part. Of which there are many many. And your plan is not even to go start a company, it's 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. Uh because I went to your website Well, you have this like list of projects. You're like I built all these things. Yeah, none of which you've heard of. Yeah, no mostly went nowhere. There's something romantic about that too. Like I'm gonna go in a cave and I'm gonna r reinvent myself. And learn this magic superpower. And I'm gonna train in the mountains where nobody's looking and then I'm gonna come back stronger. Yep.

It may not have felt that way at the time, but like I kinda knew it was supposed to feel that way. And then day to day there was some out of like I spent more than my like daily cash allowance, you know. But like I kinda knew that's what a a better version of me would feel. But practically I New I was a

person who benefits from structure and isn't always great at at 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 e this big space. in New York that was actually right across the street from the US V office. And so I got up every day and I

Got trust for my job. I mean I basically walked to the same place, but I went in a different door. And then I sat with those engineers and they were. I mean tech dress up, but it was like I did not wear the jam. Like um Yeah, yeah. And then I'd go and I'd, you know, show up in the morning and I'd like do my Uacity tutorial or try to understand Jano JavaScript to to varying degrees.

And then like go home at you know Six PM or seven PM and then often like keep doing stuff, but Basically it was like tricking myself into Acting like I had a job. So that I got up every day. I was there by 930. You know, I was just doing the things. 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 tan. And everyone was like, Where were you last week? Like basically like why weren't you at work and why are you T. And everyone being like I'm complaining for this Allen shop. I'm everything is PTO to me. Um But he was like also a like, Oh yeah, I got this. Like that's that was a kind of like a fun, fun moment too. Yeah, I 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. It takes two minutes, even though in real life it's two years.

And you have this thing written on your site that I love, this quote. And I think in my research this was my favorite. thing I pulled from 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 sores and this is from a book called The Art of Fear. Can you I love that. Can you can you explain that? Yeah, and deeply drive creative projects and I think startups or businesses or you know, internet art is all like they're all creative projects. One thing I learned at USV

Seeing seeing people bitch, but then like hearing the stories behind their big, you know Tungler, Twitter, Four Square or whatever, all the big successes of the era were When I walked into US V, I was like, everyone is Mark Zuckerberg. Not actually, but like ever and you know, like startup founders are people who have an idea visionary and they go into their room and they build it and everyone uses it. And it's like the first or second thing they've done and like Facebook picker, but that was kind of all of Mark's projects and so like that's the way, you know and like shoot. I'm like not

It's never worked for me, so I'm I'm probably not one of them. And USV was just so helpful in disabusing that notion. And being like look, some peop like a very small number of people can do that, and that's incredible. I wish I were 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. 'Cause it's both'cause it's like painful and kind of not fun and you know it's supposed to be romantic, but actually just kinda sucked hungry for two years. Literally and And metaphorically.

And it's so much nicer, but you get so much roof praise for sort of being like the brilliant person, right? And that's the expectation too. I think I just had a like well yeah, but like That's discouraging so many people from starting. It's sort of when you watch a bunch of movies about love and then you're like, This is what it's like. Yeah. I will bump into a stranger, our papers will fall on the floor. We'll swap a paper, swap a paper, he'll have to come find me. Not into him, but he just pursues me anyway. And it's like if you have that notion that that's how it goes, you'll almost count yourself out of other things that Could have worked otherwise. You know, if you 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 at the at the rodeo. We actually After I've read this quote.

On my team, we started using this phrase just called bad art. So I'll hit up my team in the morning. I'll say, 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 them I said, Imagine like You know, you go to a hotel or a motel, you're doing something, you're going to a places 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. And if you look at that and you're it's like you're mortified by it. It's disgusting. You'd turn it off right away and be like, Ew. Bad. Right. But if you No, that actually that's the process. That you sort of have this muddy water of bad ideas and bad skills at the beginning.

get it out of your system, then suddenly the water starts running clean. And I think that Framework. Is mu 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 uh And I think it was like around the chapter where that quote was. But anyway, it was an art teacher. And he said, Okay Get 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 has the best pot. And student one spends all semester crafting the perfect pot. And hand it in at the end. And student two makes two pots a day. And they're all bad for a long time, right? But over the course of the semester it hands in whatever, like

Three hundred pots. And like who gets a better grade? Right. Yeah, yeah. But it's like that concept. It's like so true. And you have to live it almost uh to really internalize it. Yeah. Actually a great um thing I did once with my company. There's Uh you've probably seen like the marshmallow test, like the psych test with kids.

It makes a good point, which is you give a bunch of supplies to uh 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 uh maybe a string and like two other things, like a piece of tape. And so the idea is hey, uh 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 wins. 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, uh You're in charge, you do the 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, we're almost time, put the marshmallow on. And the entire thing collapses because even though a marshmallow looks so small and like light, compared to spaghetti sticks. It's way too heavy. And you don't realize that'cause you didn't like

You like backloaded the possible failure, you know, the the the failure mode or or the sort of test of the of the idea. Uh, you spend all your time kinda planning and architecting 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 sticks to hold this thing up. They figure that out right away. They don't kind of save that to the end to try to perfect it. Yeah. And that sort of iterative thing about testing the riskiest assumption 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,'cause at the beginning I was just built I built a book website. It was like good reads but better, but it was actually worse because I didn't know what it was doing. And But like it was something for me. Um

This confused everyone else, right?'Cause they'd be like, Well you're Well, not you know, what are you doing without having a job? And I'm like, I'm building a book website. And they'd be like, Are you gonna compete with Amazon? No. Like, are you gonna come be with goodreads? And you're like, Well, you know, with my with my friends, but like no. You know, and then they'd be like, Well, what would you say you're doing? You know, and you're like mostly battling JavaScript errors, trying to and like spending a lot of time on Stack Overflow. You know, but anyway, this is the whole 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 bookshelf. You wanna see what's on their bookshelf. Anyway, so I was like, Okay, what if I can get everybody's books online? But he was like, clearly this is not a business. Like best case, I'm making like fifty bucks a month, you know, Amazon referral fees. Like not a business. But you did it anyways, why? 'Cause I wanted it.

I wanna and it was a good it wasn't, you know, like you do their initial coding tutorials and you like are making whatever the other person wants to make, which is not what you want to 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 shelve the books, so you live right, and then you'd like learn about CSS animations, whatever it is. And so you so you start out building stuff for yourself. Yeah.

Did you ever switch gears to Okay, now now I'm gonna do the startup startup. I'm gonna do the thing that might actually you know get me out of poverty. Like self induced poverty, basically. So at that point I was very like Look, I you know, just taught myself how to code and like, you know, am I that good? No, but Learning how to do some of this is 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, think like a computer and once you have that. Everything gets easier, but like Why we are typing on computers.

And so I kind of got on this like Uh, if we could 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 really into that personal problem. Also the like, you know Live in the future and build back you know, whatever, all the all the startup trope advice. I'm curious about that. What startup trope 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 a charmed life and like they just don't know that much. And so like what are they gonna write about?

Um And so Uh 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.

Uh, I think there's a verdict the shut your eyes, imagine the future. What's it look like build that? I think this makes sense in retrospect, I think in the moment. It's pretty hard to generate reasonable startup ideas during that. Right. But again, I can tell you a story about Vanta where Vanta fits that. And 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 Anta that Now seems to 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 was really focused on startups and sort of some new security tools. And I'm sort of like, Why? And like when does this become a ninety quadrillion like go from a zero? Tam to like ninety quadrillion dollar market size.

In precise terms. Yeah, that's the official number. Yeah, exactly. And but wait w why security?'Cause like you know, when I'm talk I've been talking to you for I don't know, twenty minutes now. You don't strike me as somebody who's like I wake up every morning and I was thinking about security during that year off. Wha why did you even think about security to begin with? Um It seemed really interesting. It seemed like this kind of competitive cat and mouse thing where they Uh with attackers where there's like kind of a real dashboard. Right. I mean one of the things I've

I mean, I guess I knew, but I didn't really know. Like I'm Very competitive. Should have played more sports if the kid didn't uh through Vanta have an outlet for a lot of that energy, which is great. And I think honestly when I was at Dropbox I worked with this product security team and they were great. They were super fun and they were really good.

educators. And it's not like they'd host, you know, seminars on things. It's just like They wanted you to fix something, but they'd come over and sit next to you and explain why it was important and how and all the anyway, they were just great. And so in coming up with structural ideas, there was a bit of like But This actually seems like a deep enough, interesting enough space that if I work in it for years, 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. Could have been worse. Yeah. Right. Like 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. Okay. 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 iterator, iterate, iterate, finally I found it. No no no, finally you found a job at Dropbox. Yeah,'cause 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 friend, they're kind of getting promoted and like I can, you know, like it's unclear if I'm employable. Like this seems bad. And I was really frustrated because again, like

I wouldn't tell people I wanted a startup to come out of that. But like I did. But I also at the time was like, Well, nothing I've worked on should be a startup. Right. So Yeah, so what was that story you told yourself? So you g you spent the two years, you bet on yourself. Yeah.

Which sounds amazing. That's a great T shirt, bet on yourself. Yeah. But the reality of it, I do it for two I told you I did it for eight years and I was delusional enough to keep going. Yeah. But also objectively. It was bad and I should have I I had to tell myself certain stories in order to either keep going or to like just

Maintain a self of c a sense of confidence. Beyond that because the evidence was telling me you suck. Yeah. Yeah. And I just couldn't tell myself you suck,'cause then I definitely suck. Yeah. What were you saying when the evidence kinda said You suck. This was very silly.

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 are you gonna do? Like, what's your next goal? What are you gonna do to move forward? You made that for yourself. Made 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 up mattering 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 keep going. But my past self sometimes things current self should stop, right? And so it's 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'm at now. I don't actually think I have countervailing evidence, I just have stubbornness. Shoot. I should probably stop. And so that's how you were stopping those projects. 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, uh managing your own psychology. Is

One of the most important things. Yep. Um, how does one 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. Um, 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 it was like um you know running three or four times a week. And like exercise, sure, but it was actually just like the mind clearing catharsis kind of meditative, like running. And Yeah, 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 what you're talking about is habits and hobbies. Is that more of what you're thinking about? It's just like that feeling where you like you're you're like moving through the world and you like feel like you're at your best, you know, like you're the best shiniest version of yourself. It's like What brings that on? So for you running is one, what is one.

Reading? Like not in any I mean kind of an elegant intellectual way, but actually just because it is something I have done since I was six years old. Right. And so like If I think of like hobbies or anything I've done through my life, reading is actually one of the biggest through lines.

And so there's a part of that that just feels like me. Yeah,'cause 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 I mean yes, I'm gonna learn things and like blah, blah, blah. But actually it's just like it is centering How do you do that? When I was running a company and and by the way, mine was not a two point four or five billion dollar company. I was like, I have no time to read, are you kidding me? There's problems everywhere. I'm drowning in problems. And Did you just replace TV with reading or something as simple as 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 book. And read the whole book on the bus ride. Oh but yeah, I mean over the course of a week or so. But yeah, like uh actually to this day. The way he said it was more legendary. He was like to and from cover to cover. No. I can actually I actually still take a bus to work part of it. So I can just sit there and like you bust to work. Yeah. 'Cause if I take a car, I'm just gonna like sit in the back with my laptop writing emails, you know. Uh and in a bus, like I'm San Francisco bus, I'm not pulling on my laptop on that. Unless something's like really gone wrong. Um, and so it just forces me to like sit there and have twenty minutes between home and work. Um and I like that. It's almost like you know people are like obsessed with cold plunges. Yes. I think the more hardcore version is take a San Francisco bus to work. It's like wow, you can endure a eighteen minute bus ride with like the buses aren't bad. Five R used to be my bus. Five R is a great I used to take the thirty eight and the thirty eight is like a actual zoo. It's like it's anything can happen. Yeah, yeah, yeah. No five R great bus. I miss it.

I'm that's right. So Banging or Psychology said uh Figure out what makes you feel like you, most you. And make sure you stick with those things, keep doing those things. It'll kinda keep you you centered with it. What about

Bandage your own psychology when it comes to self doubt, when it comes to getting down on yourself'cause 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 story you told yourself in order to to Yeah, I was so annoyed. I was s which in retrospect, I was like being so pretentious. Like life was good. You know, again. Like the

The Batna, like my worst case outcome with becoming a product manager at Dropbox. I drop boxes power. Like my life was great. Could you just say the bat nut? Yeah, right. But like my life was great. It did not feel great at the time. It was totally great. And again, I knew I was like five percent aware of that, ten percent, but that was not the lived feeling. Do you use negotiation terms like that just regularly? Hopefully not that sounds kind of obnoxious. I'll try not to. No. No, I like that. I've always felt that if you build a great Silicon Valley company, internally in your company, you 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 extra valuation. It just creates this extra aura. Wow she's she's barefoot all the time. Wow. Interesting. She must be one of those real outlier types. Oh my gosh. I wanna ask you about this list of ideas that you did. So I've looked back in my career and

Even when I wrote Eras where I tried something and it didn't work. A lot of the times I look back with the benefit of hindsight now and I think oh I was just sort of an idiot about it. Had 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 of the projects you worked on? Um like they're art projects and I say that with deep love, but like they're not businesses. Okay. Um The voice assistant for biologists. Yeah, that doesn't sound like a great. That was just comically 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 Vanta has had commercials.

like baked in from the very beginning'cause I'd made that mistake 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, uh, maybe like parts of the market that are unaddressed.

If somebody's 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? Yeah, I think

So so much of What I think about that's not kind of directly invented wheelhouse is something around like running a B2B SAS or being in a B2B SAS business, forget running it, just being in it. There's like so m like someone please fix the go to market tooling stack. There's nine thousand tools and none and it's like you jerry wig to them together in this Rube Goldberg machine and the marbles are all over the floor and like Anyone wants me to be fast, just like fix that.

Go full stack on all that. But for people who don't want me to be fast, which there are hopefully many. I think the Crossed Vanta came out of I mean, I of course like I mean I liked it going in, but now 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 of the space. The story I heard about Vantap which

Sometimes we make up these retrospect stories. So I I don't know you tell you can I try to actually tell the the true one. Like blink twice if it's true and But it was you're at Dropbox, you work on this thing called paper, which was this I remember like seeing paper at the time was like this idea of this like collaboration tool. And you go to one of the boys Google Docs. Yeah, Dropbox is Google Docs. You go to launch it and it's like, Hey, we don't have Stock Two, 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. Yeah. Dropbox had a security team that was gonna be able to Try to solve those problems, but like the average startup doesn't. Yep. 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 coded 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. Yeah. And you went to one or two startups, 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 true.

The stylized part is all the Dropbox stuff happened. There was no light bulb. I was like not smart enough to have a light bulb go 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. It just sounded awful. Especially when we were 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 have product market fit. You're like Bad.

Bad. Like how do I find reality faster? came back to it later, did the spreadsheet thing. And I think honestly it's like'cause there's certain five things on the list. Like kinda the point where you're like, okay, I can write, you know, maybe somewhat shoddy JavaScript, 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 like they hear you should talk to customers, you should validate if 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 how Who do you talk to? Yeah. What do you 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 maybe I'd be interested. Um, 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 want to be kind, and so they don't say like rarely do they say no. But a lot of like, oh, maybe next quarter, like I don't need this, but my friend might hard nose. Yeah, you should take my friend. Hard nose. Totally. Hard nose.

Um I think on who to talk to. I mean like we started with like anyone who would talk to us and then it was just like And then so it ended up being co workers, former co workers'cause you had

Like some like Well I don't know if you know anything about this topic, but you're kind of a nicish 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 it you know You ask them, Do you have anybody else? and they've less people and like Say yes, follow up with customized email, second forward, you know, like make it easy for them.

And just keep going out. Yeah, I think that's an important one. Make it easy for them to do the thing they said they want to do. Oh yeah. Like follow up 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 assume they will. Like write them an email they will forward. Exactly. So you um Have you ever read this thing called the Mom test? Yes. Uh do you

Subscribe to that. Yeah. Yeah, they uh That was helpful to me when it was only 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 problem. So all your questions need to be first about their problem.

And then At the end if you want to ask them about the s about your solution, great. But Just assume they don't really know the what the solution needs to look like. Yeah. I think that's true. Try to avoid yes, no questions. Oh, just harder than it sounds. And there's a bunch of kind of user research.

Tips, tricks of like if somebody mispronounces something, go with their pronunciation. Otherwise they're gonna like don't break rapport. Exactly. Exactly. Like a lot of things. I think I do that. And it 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. Oh, am I am I being stupid? Did I 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 Vanta kinda got the flywheel going? Cause Yeah, startups don't kind of less like explode right away necessarily. Yeah. And I've seen your like ARR chart, which looks like a beautiful hockey stick. But if you zoom in, it's like wow, that was a year where it's like pretty kind of small. And then Then it started to accelerate. Was there anything you did that you thought was

Interesting, unique. Um That kind of It's so funny looking back'cause Like I sent a bunch of outbound emails to I C companies, but I didn't know the word outbound. At the time.

Right. I was like emailing YC Founders 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 it. And then the end be like, I am building a thing. Would you like to hear about it?

But it was like totally called outbound. You know, I just like didn't know that word. So you emailed a bunch of Y C 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 mouth. We tried actually really hard in the early days to

basically build this call response in like founder Slack channels or VC Slack channels where someone said SOC to and someone else would say Vanta. And you just wanted this, you know. You're saying like build the brand in people's minds. Yeah. And that was great for a while. And then Uh Bunch of knockoffs came and uh there's a bunch of other ways you could talk to. And so that that association

I remember you guys had the billboard. But is it compliance that doesn't sock too much? Yep, still up. Still up. Um Uh yeah. joke with people, like we make software, but like we also make a billboard and we're equally known for both of these equally as important. Um

What else? Uh podcast advertising. really worked in I mean actually it still really works, but like really worked in the early days. I thought podcast advertising were just gonna be like sending money out the window. I was totally wrong. And that's what happens. Somebody on your team pitches you this. Uh Eric pitches you. Eric was like I want Twenty K go on Twit this week in startups or something and I like rolled my eyes.

And said fine, whatever, go. You totally were, she was totally right. Eric is like this mythical favorite to me now where I've only ever heard great Eric stories. And so I don't want to hear any if anybody has a bad Eric story or a an idea you had that didn't turn out true, don't tell me, please. No. I want to ask you about a couple other Of your

Controversial or maybe just less um 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 is on your website. Oh yeah, and people read a lot into this. I'm just like joking with myself because I say contact me through these four waves that are all have totally different names on them. Yeah, it's just like minor self awareness um thing that I think people think is meant to be a broad philosophical statement.

To actually think of the broad philosophical statement. No, probably not. I think Vanta's taught me consistency is Actually underrated. Yeah, I was gonna say you strike me as somebody who's consistency first. Yeah. Um It's bad it's bad when the goalposts move. I don't know if you're saying you think this or that other people think this. You know, if your goalposts keep moving, it's hard to ha find happiness and like you're always thumping in. What what does that even mean? Like uh I mean I mean get to bot in lots of forms of life, but like let's take startup founders just'cause

Right. You wanna start a company You wanna hire some people, you wanna wait the seed round, you wanna get to like a million an error, but then by the time you get there, you're like actually I wanna get to ten, right? Like Yeah, that's 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 that can be true in some cases, but I actually think or I think that

The the trick is slash downside is if you're like Only happy uh when you hit a goalpost. And then you're moving them, like you'll never be happy. She actually just like the work. Right. So it doesn't matter.

And I think 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, it's 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. Cause 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 happy. Right. Right. When in actuality it's just a sense of progress. I even better. A sense of progress in a direction that you have set out intentionally that you care about. Yeah. Um and I think that In that sense. Moving the goalposts 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. It's a different way of looking at it. Do you remember

Deep cut. Ten, twelve years ago, Jess who that founder of Polyvore at the time now. So Koya wrote a blog post about founder psychology. No, what would it say? It was like why basically like why our founder is always unhappy. And

She's like, especially when their companies go like this and it was a line up and to the right. And like because of you Zo, you know, again, Y axis getting higher. Like what is this? Yeah,'cause 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 every time. Yeah, it's the peak to trough that that you feel. You don't really even recognize that you've gotten higher progressively each time.

You also have another one, which is high stand high standards are bad. You think that In generally you said people don't say this. Yeah. Yeah, don't have such high standards. Uh. What is w what's the situation where that's come up for you or you felt that I think a lot of

Vanta stuff and I think within the company and then with, you know, kind of partners or 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, again, something might have gone wrong, but the person tried really hard to fix it. Right. And I think

Those things definitely don't. happen. Everywhere by accident. It's not to say I had I mean Pro hopefully a small role in it, but I think

When people join, there's a little bit of like oh the bar is here at Vanta. Like Kind of scary. Did I die in the right place? Like what's going on? What's an example of that? Wh where would somebody feel that? A couple of places, but I guess in go to market are Expectations around quote or around attainment on that there

Way off. industry. They're way higher. And I think if you just if one just hears them in the 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, Oh,'cause you're surrounded by people who are like Into what they do, getting better every day, want to get better every day, care a lot. And that sort of environment can be like really infectious. I'm curious, did you ever read this? leaked production document from Mr. Beast. Did you ever take a look at that? Did you see that going around like a few weeks ago? I know.

You know the Mr. So like right around the same time that Paul Graham put Founder Mode out there and everybody's like, Oh, Founder Mode like But wait, what is it exactly? And like I think yes, but what what? Um part of a lawsuit, Mr. Beast like D internal doc he wrote for his production team leaked.

a big part like we've gotten to know him and become uh you know pretty friendly with with Jimmy over time and It's just stun like the the number one thing, you go hang out with Jimmy for a couple of days, like You walk away and you're like Oh, he that's what people that's what it means when people say real you know, Steve Jobs used to have this reality distortion field. Yeah. And it's and literally he he

His company's 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 Like one of his things is like 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 um You know, we asked for the permit and they said it's gonna take six months.

Like that can't be the end of the story. And I we saw it on every little thing, like for example We wanted to play basketball the next day and it was midnight. And somebody was like, Oh man, I can't wait till tomorrow. Like I just want to play. He goes, Well, why do we have to wait?

Like well sp midnight. Jimmy, what are you gonna do? He's like, I'm sure there's a gym around here somewhere. Let's go let's go find one. And uh we're like, Yeah, but they're gonna be locked. It's midnight, like schools aren't gonna be open. He's like, call the athletic director. He's like, just call all call all of them right now in the in the county. It'll take us twenty minutes. And offer any of them a thousand bucks see if they'll come open it.

And like Part of it was like oh he just throw money at every problem but Actually it's not about throwing money at it. It's Yeah. Everybody else would immediately just default to like just not possible, not feasible, not not gonna be doable. Whereas his default assumption on any any given thing is like why not? Of course we could do that. Yeah.

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 gear. It's like, Oh, your gear is like My s my stick shape only goes to six. Yours goes to nine. Okay. If 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. Yeah, w this won't be the right place for me. Yeah, totally. And I think there's a Uh I mean I think If you like experience that and you're like, you know what, I'm go with six. Right. Totally reasonable decision. Like

Not that you know. ar arguably maybe a better decision in some case. It's like totally fine, but the So like there might be there might be a nine. Um 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 A R R 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.

Um, but more so when you went to go do it. What was that experience like?'Cause you had leverage. Yeah, it was great. Um it was really funny. So people n or VCs in San Francisco broadly like knew we were doing well because of kind of the slack channel chatter, like Advantage Come Up. They sort of didn't know how well. And so there was one pitch meeting I remember they And sorry, you kept it low key right on purpose. Cause we were like, We have this. Great idea and everyone else thinks. They can't even like spell what we're working on.

think it you know, has K's and to do things on your feet. And I would rather they not know,'cause then somebody's gonna start knocking this off and copying. But you know what? Very smart V C. Very good at his job.

Like go and pitch and I start walking through the slides. And I get to the error ramp chart that you know. ten at the end of it, basically. And his jaw just drops. And he was like clearly speechless. And he's looking at it and he's like, I Thought you were at like two and a half.

Um and you're like no that that was you know the the you know ten anyway like Keep going. And at the end it was sort of like we're like not gonna like we missed it. Like we're not gonna be able to do this. Um I can like try to introduce you to someone else, but like, you know. It was fun like fine, like, you know, there were other people, but it was this kind of interesting pitch experience. Um and then basically I go into a meeting with another DC was he was very good at his job.

And he's like, You know what? Thought you were at nine point four. Cause I'd like taken your Twitter chart and backed it out and like counted the pixels. And I was like putting your own. I did the proportions. She said ten. So if this is ten, where was she a year ago? Two point seven or whatever. He had basically done that. And that was also you're like, Oh, it's great. It's so good at your job. So fun. Is that who you end up going with or no? Uh no. You're great, but Sequoia's calling. But I think actually it was

Still the goalpost stuff and I'm you know not very good at telebrating, but it was a moment where it like took a I mean a beep like a week. And I was like, No, I am gonna like tell this story and what we've done and like I'm deeply proud of it. I would have told you that, but now I like feel overwhelmingly proud of it, right? Um and like here's how the pizzas fit together, here's how they will fit together, and I believe it. And so that was just then it became like

Uh I thought kind of hate fundraising, but It was talking about something I believed in. It's fun. Right.

Eric told me that You think you're great at negotiating. You said you said uh that that's surprising to you. But he w he was not uh He was not wishy washy about it. He's like, She's incredible at negotiating, one of the best I've ever been around. Ask her how or why she does it. So no pressure. Yeah, no, it's like really surprising. I think If I'm confident in it, I'm ac actually confident in it, and then we'll just stand and like Not blink, not swerve if we're playing chicken, won't 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 throw on weight at that point. So I think it's just a lot of that. Like a If I believe it, I won't flinch.

Cool. Well thank you for doing this. This has been amazing. Um Where should people, you know, find you, find vanta, maybe give it a shout. Yeah, uh vanta.com, V-A-N-T A.com. Um If you need any help with anything security or compliance related. Love to help you out. Awesome. Thank you for doing this. Thank you so much. I feel like I can rule the world, I know I could be what I want to.

I'm putting my law in it like my days off On the road less travel never looking back

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