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

And at the time, my email was christina@usv.com. And it was like, the right side, that usv.com, is way more powerful than the left side. And now you are giving that up. And so 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?

I feel like I could rule the world. I know I could be what I want to. I put my all in it like no days off. On the road, let's travel.

Never stop.

I don't know if you know this fun fact. Do you know what you, Katy Perry, and Serena Williams have in common?

Oh, God, nothing.

You're all on the Forbes Self-Made Women on the List.

I hate that list.

And you are ahead of them. Isn't that kind of amazing?

I would have preferred that list never existed. Yes.

You have that Midwest modesty.

Yes. You're like, nothing good will come from that list.

Yeah, yeah, yeah. Those lists are, they're sort of made for the wrong type of people. Yes.

Or jail time later or something. I don't know why I laugh at that. I was never on 30 Under 30, and I'm deeply glad about that now.

I would say stumble hustled. Okay.

I didn't like the job.

And I read something that was like, they, maybe Fred or somebody at the USV team was telling you, you should specialize in crypto, you should become a crypto VC. Is that true?

Kind of. It was actually when I was leaving. So this was end of 2012. I had a lot of angst because this job was great. They were great, you know, like, haven't you made it? And I was sort of like, eh, but I don't think I like it. And again, What's going on? And one of my hangups was, uh, you know, what have I done? Why would anyone take my money? Right? Who's going to take a check from me versus, in my head at the time, Matt Kohler, this, uh, GP who's no longer at Benchmark but had this, like, illustrious Silicon Valley career of, like, LinkedIn, Facebook, Benchmark. You know, and you're like, me versus Matt Kohler, everyone will choose Matt Kohler, like, 100 out of 100 times.

Which is, let's say, maybe a part partially imposter syndrome, but also maybe hyperlogical also.

Because you didn't believe in crypto or you were just like, that's not me.

I was just like, I don't know if I wanna be an investor.

Okay.

Even though it's great and it's wonderful and it's 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 was so anxious.

Was everybody patting you on the back and saying, you're gonna make this happen?

Definitely not. What I did and what my plan was, was I'd saved my bonus from the prior year and I was kind of like a finance bonus, and I was going to 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, because 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 2 years at USC 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, investors— 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— no one leaves USV 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? Because clearly you don't know what you want to do. And then some amount of, like, kind of the tougher stuff, I think, where a couple— one person in particular I had been close to and who was very like, there's the left side and the right side of your email address. And at the time, my email was christina@usv.com. And it was like, the right side, that usv.com, is way more powerful than the left side. And now you're giving that up. And so 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 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 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 it—

like, I kind of knew it was supposed to feel that way. And then day to day, there was some amount of like, I spent more than my like daily cash allowance, you know? But like, I kind of knew that's what I— a better version of me would feel. But practically, I knew I was a person who benefits from structure and isn't always great 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, this big space in New York that was actually right across the street from the USV office. And so I got up every day and I got dressed 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 would share stuff.

Did you actually dress up, by the way? Because I feel like there's psychologically something to actually dressing up. Totally. Oh, yes. Totally. —like you're going somewhere.

Yeah, I think it's deeply true of creative projects and I think startups or businesses or, you know, internet art is 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, Tumblr, Twitter, Foursquare, or whatever, all the big successes of the era were— when I walked into USV, I was like, everyone is Mark Zuckerberg. Not actually, but like everyone, 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, bigger, but that's kind of all of Mark's projects. And so like That's the way, you know? And, like, I'm kind of like, "Shoot. I'm, like, not— it's never worked for me, so I'm probably not one of them." And USC was just so helpful in disabusing 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 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 5, and it might be thing 55. But no one really talks about that because it's both— because it's, like, painful and kind of not fun. And, you know, it's supposed to be romantic, but actually it just kind of sucked. Hungry for 2 years, literally and metaphorically. And it's so much nicer— like, you get so much 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 like 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, he'll have to come find me, but then I'm not into him but he just pursues me anyway. And 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. And 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, uh, you know, at the rodeo. We actually, after I 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. 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 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. And if you look at that and you're— it's like you're mortified by it. It's disgusting. You turn it off right away and be like, ew, bad, right? Leave. But if you know 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, is just very useful for anyone who's doing either creative endeavors or startups, which are a pretty creative endeavor too.

Less the very beginning, because at the beginning I was just building— I built a book website. It was like Goodreads, but better. But it was actually worse because I didn't know what I was doing. And, but like, it was something for me. This confused everyone else, right? Because they'd be like, well, you're 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 compete with Goodreads? And you're like, well, you know, 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 anyways, this is a 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 it was like, clearly this is not a business, right? Like best case I'm making like $50 a month, you know, Amazon referral fees, 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 their initial coding tutorials and you like are 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 an animation when you shelve the book. So you, right. And then you'd like learn about CSS animations, whatever it is.

And so you, so you started building stuff for yourself. Yep. Did you ever switch gears to, okay, now, now I'm gonna do the startup startup. Yeah. I'm gonna do the thing that might actually, yeah. You know, get me out of poverty, like self-induced poverty basically. Yeah.

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 our programming tools make us like hold everything in our heads, and you have to teach yourself to think like a computer and like read through code, which is like not how a person— you know, you 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 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 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, "Write what you know," and then you, like, you know, it's like a 14-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? And so my version of that is, like, look, if there is something personally meaningful, like, by all means go for it. Right.

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 ver— 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 I can tell you a story about Vanta where Vanta fits that. Yeah. 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 Vanta that now seems obvious, as all great ideas do once they exist. Now there's you guys and 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.

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 startups didn't use security tools. And I was sort of like, why? And like, when does this become a $90 quadrillion— like go from a zero TAM to like $90 quadrillion market size in precise terms.

Yeah, that's the official number. Yeah, exactly. Um, but wait, why security? Cause like, you know, when I'm talking, I've been talking to you for, I don't know, 20 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. What, 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 think 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 as a 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 hosted, 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 startup ideas, there was a bit of like, well, 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, 18 months of my life learning about security on the internet, could have been worse. Yeah. Right? Like you kind of 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.

Well, connect the dots for me. So you, you took the year or multiple years off to teach yourself, 2 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 iterated, iterated, iterated, finally I found it. No, no, no.

Finally you found a job at Dropbox. Yeah, 'cause I was kind of like, okay, now I can code, but I've never had a real job. I've never worked at a company. I've never worked with people. Also, my, my like friends are kind of getting promoted and like, I can, you know, like it's unclear if I'm employable. You know, like this seems bad. And I was really frustrated because again, the, 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 like, yeah. So what, what was that story you told yourself? So you, you spent the 2 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 you I did it for 8 years. Yeah. And I was delusional enough to keep going. Yeah. But also objectively, it was bad and I should have— I had to tell myself certain stories in order to either A, keep going, or to, like, just maintain a self— a sense of confidence beyond that because the evidence was telling me, "You suck." And I just couldn't tell myself, "You suck," because then I definitely suck. What were you saying when the evidence kind of 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 are you gonna— like, what's your next goal? What are you gonna do to move forward?

You made that for yourself?

And so that's how you were stopping those projects. Yeah. You— when we— I sent you some questions ahead of this to try to understand 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. Yep. 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?

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?

Yeah, 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 else? Running was 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 6 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. 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 30, 50 books a year or something.

Yeah, but it's, it's like, I mean, yes, I want to 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 by the way, mine was not a $2.4 or $5 billion 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, 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, nah, to and from, COVID to cover.

No, I wasn't it. I 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? Uh, and then a bus, like, I want San Francisco bus. I'm not pulling out my laptop on that unless something's like really gone wrong. Um, and so it just forces me to like sit there and have 20 minutes between home and work. Um, and I like that. It's almost like, you know how people 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 an 18-minute bus ride with like—

Some of the buses aren't bad. 5R used to be my bus.

5R is like great. I used to take the 38 and the 38 is like an actual zoo. It's like, it's— anything could happen.

Yeah, yeah, yeah. No, 5R, great bus.

I miss it. I miss it. Okay. So, um, so banjo psychology, you 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 kind of keep you, you centered with it. What about then is your own psychology when it comes to self-doubt, when it comes to getting down on yourself? Because I spent 2 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—

Yeah, I was so annoyed. I was, 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 was becoming a product manager at Dropbox at the height of Dropbox's power. Like my life was great.

Did you just say the BATNA? 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 5% aware of that, 10%, 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 10% crazy. Yeah, it just gives you like actually like 2x the valuation. It just creates this extra aura. Totally true. Wow, she's barefoot all the time. Why? Interesting. She must be one of those real outlier types. Oh my gosh. All right, I want to ask you about 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 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?

No. 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 business.

That was, that was just comically bad. No. Yeah. There was 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, um, maybe like parts of the market that are unaddressed. If somebody's listening to this right now and they are looking for 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?

The story I heard about Vanta, which sometimes we make up these retrospect stories. So I don't know, you tell, you can—

I try to actually tell the true one. Like blink twice if it's true and whatever.

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. Dropbox is version of Google Docs. Yeah, Dropbox is Google Docs. You go to launch it and it's like, hey, we don't have SOC 2, so can't really launch or customers can't use it. And you were like, SOC 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 going to 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 2 years learning to code and built 35 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. Yep. And you went to 1 or 2 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?

So I, I think a lot of people hear that and they're 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, 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.

Yeah, I think that's true. Try to avoid yes/no questions, uh, which is 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 times 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 at you basically. Yeah, exactly.

Do you have any good hustle stories for how Vanta kind of got the flywheel going? Because, you know, startups don't kind of just like explode right away necessarily. Yeah. And I've seen your like ARR chart, which looks like a beautiful hockey stick. Yeah, totally. 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 felt was interesting, unique, um, that kind of took hustle or creativity?

It's so funny looking back, 'cause 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 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, 60, 70% of the call Talking about the problem and how you're solving it, and then in the end be like, I 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 emailed a bunch of YC people. Yeah. 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 SOC2 and someone else would say Vanta. And you just wanted this, you know, SOC2 or Vanta.

You're saying like build the brand in people's minds. Yeah.

And that was great for a while. And then, uh, a bunch of knockoffs came and there's a bunch of other ways to get SOC2.

And so that, that association, I remember you guys had a billboard that was like, uh, what is it? Compliance that doesn't SOC too much. Yeah. Still up. That was good.

And that's what happened. Somebody on your team pitches you this?

Eric pitches you this? Eric was like, I want, 20K, go on Twit— This Week in Startups or something. And I like rolled my eyes and said, fine, whatever, go. It totally worked. She was totally right.

Eric is like this mythical figure to me now where I've only ever heard great Eric stories. And so I don't wanna 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. All right. I wanna 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 why. Consistency is overrated. This is on your website.

Oh yeah, people feed a lot into this. I'm just like joking with myself because I say contact me through these 4 ways that all have totally different names on them.

Oh, okay.

So like, it's just like minor—

Naming consistency is overrated.

Yeah, it's just like minor self-awareness, um, thing that I think people think is meant to be a broad philosophical statement. Do I actually think it's a 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.

I think other people do. The advice tends to be, right, like, you know, if your goalposts keep moving, it's hard to find happiness and like you're always something more.

Explain what it means. So like, what does that even mean? The goalposts moving?

Yeah, like, uh, I think, I mean, it gets applied in lots of forms of life, but like, let's take startup founders just because, right? It's like you want to start a company, you want to hire some people, you want to raise a seed round, you want to get to like a million in ARR, but then by the time you get there, you're like, actually, I want to get to 10, right? Like, yeah, yeah. And there's like always something you are chasing. And I think that is 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 trick is— slash downside is if you're like only happy when you hit a goalpost and then you're moving them, like you'll never be happy. If you actually just like the work, right? So it doesn't matter. And a lot of things are more sustainable when you like the work, especially when you have a lot of work to do.

Good. My formula is progress equals happiness, which is that no matter where you are, it's sort of like 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 happy. Right, right. When in actuality it's just a sense of progress. Even better, 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 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. Yeah, it's a different way of looking at it.

Do you remember, deep cut, 10, 12 years ago, Jess, who was the founder of Polyvore at the time, now Sequoia, wrote a blog post about founder psychology?

No. What did it say?

It was like, why— basically, like, why are 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— you know, again, y-axis getting higher, like, what is this? You know, because if you zoom in on the graph, it doesn't look like a, you know, 45-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 45-degree line, the downs hurt every time.

Yeah, it's the peak to trough 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 standards are bad. You think that in generally, you said people don't say this, but they imply it in different ways that, you know, don't have such high standards. Right. What is, 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 know, 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 tries 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, probably 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 join the right place? Like, what's going on?

What's an example of that?

Where would somebody feel that? A couple places, but I guess in go-to-market, our expectations around quota, around attainment, on that, they're way off industry. They're way higher. And I think if you just, if one just hears 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, 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 MrBeast? Did you ever take a look at that? Did you see that going around like a few weeks ago? I know.

Do you know what this is?

Yeah. So like right around the same time that Paul Graham put Founder Mode out there and everyone's like, oh, Founder Mode. Like, but wait, what is it exactly? And like, you know, it was like, I think yes, but what? Um, part of a lawsuit, MrBeast's like 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 stunt, 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 reality, you know, Steve Jobs used to have this reality distortion field. 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 6 months. And he, like, that can't be the end of the story. And 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. And he goes, well, why do we have to wait? Like, well, it's midnight, Jimmy. What are you going to 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 like, yeah, but they're going to be locked. It's midnight. Like, schools aren't going to be open. He's like, call the athletic directors. He's like, just call, call all of them right now in the county. It'll take us 20 minutes. And offer any of them $1,000, see if they'll come open it. And like part of it was like, oh, he just throws 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, this is not possible, not feasible, not, not going to be doable. Whereas his default assumption on 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 you just see that time after time after time hanging out with him 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, my stick shift only goes to 6, yours goes to 9. Okay. Right. If I'm gonna hang out with you, I now need to decide like how I'm gonna get to 8 or 9. Yeah. Because otherwise I'll just be sticking out. Yeah. This won't be the right place for me.

Yeah. Yeah, totally. And I think there's, uh, uh, I mean, I think also if you like experience that and you're like, you know what, I'm go with 6. Right. Totally reasonable decision. Like, Not that, you know, arguably maybe a better decision in some cases, like totally fine. But the, the like, there might be, there might be a 9, um, for any given thing. I think it's a helpful mindset.

Yeah, it was great. Um, 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, like Advanta had come up, but they sort of didn't know how well. And so there was one pitch meeting.

I remember what they— and sorry, you kept it low-key, right?

Yeah, I did the same, actually. And, like, counted the pixels.

And I was like, you're good at your job.

I did the proportions. Totally. I was like, she said 10, so if this is 10, where was she a year ago? Get 2.7 or whatever. Totally.

He had basically done that. And that was also, you're like, oh, this is great. So good at your job. So fun.

Is that who you end up going with or no? Uh, no. Look, you're great, but Sequoia's calling.

See ya. Um, no, but I think actually it was still the goalpost stuff and I'm, you know, not very good at celebrating, but it was a moment where I like took a, I mean, a beat, 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. And I would've told you that, but now I like feel overwhelmingly proud of it. Right. And like, here's how the pieces fit together. Here's how they will fit together. And I believe it. And so that was just— then it became like, I still kind of hate fundraising, but it was talking about something I believed in, which is fun. Right.

Eric told me that he thinks you're great at negotiating. You said— so funny. You said that's surprising to you. Yes. But he was not wishy-washy about it. Yeah. 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 actually surprising. I think if I'm confident in it, I'm like 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 sit there and wait at that point. So I think it's just a lot of that. It's like, I won't, 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, vanta.com, V-A-N-T-A.com. If you need any help with anything security or compliance related, we would love to help you out.

Awesome. Well, thank you for doing this.

Thank you so much.

I feel like I could rule the world. I know I could be what I want to. I put my all in it like no days off. On the road, let's travel, never looking back.