I failed 22 times... then I built a $2.5B Company

And at the time my email was [email protected], and like the right side, that USV.com... and like, what do you think will happen?

Here, um, do you know what you, Katy Perry, and Serena Williams have in common? You're all on the Forbes self-made women list, and you are ahead of them. Isn't that kind of amazing?

I would've preferred that list never existed. Yes, you have the Midwest modesty. Yes, nothing good will come from that list.

Yeah, yeah, those lists are, um, they're sort of made for the wrong type of people. Yes, um, or jail time later or something.

I laugh that I was never on 30 Under 30, and I'm like 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 got a cool office in San Francisco. Last valuation, I believe, 2.45 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 going to put that out there, that might be true or might not be true, but the basics of it is 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 want to do, but they don't take the leap. You took the leap, and it's not like it hit right away. And you created Vanta, and you created this, you know, multi-billion dollar company right off the bat. You did like 35 things wrong, uh, or 35 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 kind of hustled your way into.

I would say stumble-hustled. They announced that job like they do all their 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 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 them, 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 was it?

Twitter, Flickr. See the era of this. And I had started a design blog a couple months before, and I lived in Berlin because I wanted to be like a designer who lives in Berlin, and those people seem to have design blogs, so I started one, and that was it, and they hired me, which is crazy.

And I read something that was like, 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. 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 sort of like, but I don't think I like it. And again, 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 going to take a check from me versus in my head at the time, Matt Cohler, who is no longer at Benchmark, but had this like illustrious Silicon Valley career of like LinkedIn, Facebook, Benchmark. You know, you're like, me versus Cohler, everyone will choose Cohler like 100 out of 100 times, which is, let's say, maybe partially imposter syndrome, but also maybe hyper logical. Also I think like, yeah, but like also true. Anyway, and I basically said that to Fred. He said a couple things, uh, deeply insightful. One was like, well, you know, 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, and he's sort of like, look, I've seen you in the office for two years, worked with you for two years, like you're not going to be going to, 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 2012, I recommend you choose crypto. Really good advice on a bunch of dimensions. 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 VC, but like I want to go make things. So you decided to go make things. Take me back to that decision. Was that easy?

No, I was so anguished.

Was everybody patting you on the back and saying you're going to make this happen?

Definitely not. What I did, what my plan was, was I'd saved my bonus from the prior year, and it was kind of like a financial 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'm 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 two years at USV 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 the office, investors, 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 specific, 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 one person in particular I'd been close to, and who was very like, just the left side and the right side of your email address. And at the time my email was [email protected]. 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?

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 going to teach yourself how to code by going 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, like I built all these things, yeah, none of which you've heard of.

Yeah, mostly went nowhere.

There's something romantic about that too, like I'm going to go in a cave and I'm going to reinvent myself and learn this magic superpower and I'm going to train in the mountains where nobody's looking and then I'm going to come back stronger.

Yep, it may not have felt that way at the time. I kind of knew it was supposed to feel that way, and then day to day there was some element of like, I spent more than my daily cash allowance, you know, but like I kind of knew that's what 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 it for myself. So what I did was a friend of mine had just sold a company to eBay New York and opened up 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.

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

I did dress up, but it was like, I did not wear pajamas. 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 Audacity tutorial or try to understand JavaScript to varying degrees, and then like go home at, you know, 6 p.m. or 7 p.m. and then often like keep doing stuff. But basically I was like tricking myself into acting like I had a job so that I got up every day, I was there by 9:30, you know, I was just doing the things. 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 tan? And I'd be like, I comped for this, like everything is PTO to me. Um, but it was like also like, oh yeah, I got this. Like that was kind of like a fun moment too.

Yeah, I like that. So you have this era which is kind of like in the movies, it's the montage, they just fast forward through this part, takes two minutes even though in real life it's two years. And you have this thing written 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 soars. And this is from a book called The Art of Fear. Can you explain that?

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 people, but then like hearing the stories behind their big, you know, Tumblr, Twitter, Foursquare, whatever, all the big successes of the era, 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, vision, 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, Twitter, but I was kind of aware of Mark's projects, and so like that's the way, you know, and like I'm like, shoot, it's never worked for me, so I'm probably not one of them. And USV was just so helpful in disabusing that notion and being like, look, 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 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 just kind of sucked, and like hungry for two years literally and metaphorically. And it's so much nicer, like you get so much more 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. 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, but then I'm not into him, but he just pursues me anyways. 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 a vision, does it, takes off, and then he rides that bull at the rodeo.

All right, so when I ran my company, The Hustle, I think we had something like two million subscribers, and we made money through advertising, and we didn't actually make that much money per person reading the newsletter because advertising in general is kind of a crappy business model. And so I remember sitting down and I'm like, what are all the different ways that I can make money off The Hustle that aren't advertising? And so to make sure that you don't make this mistake, Shaan, me and the HubSpot team, we went and looked at a bunch of different ways to monetize your business, and we put it all together in a really cool document where we lay it all out along with our research, and we called it, very appropriately, we called it the Business Monetization Playbook. Go to the description of this episode and you're going to see a link to that Business Monetization Playbook. It's completely free, you just click the link and you can see it. Back to the episode.

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. 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 it. 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 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 that quote was, but anyway, there was an art teacher and he said, okay, art school pottery class, you have one assignment all semester. You have five weeks to make the perfect pot. You can turn in as many pots as you want, but I will judge them all, and the highest grade will go to the person who has the best pot. And student one spends all semester crafting the perfect pot and hands 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? Of course, three hundred, right? Yeah, yeah. But it's like that concept, it's like so true. You have to live it almost to really internalize it.

Actually, a great thing I did once with my company, there's, 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, you break your team into a bunch of groups, groups of maybe four or five, and they get like sticks of spaghetti, one marshmallow, and there's something like maybe a string and like two other things, like a piece of tape. And so the idea is, hey, you have an hour. At the end of the hour, I will come around, I will measure whoever from the tabletop has the highest marshmallow. So whoever could build the biggest tower 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 kind of like, okay, you're in charge, you do this, you sort of segregation of duties. You start trying to like plan, and then you sketch a little bit, then you start building the tower. And at the very end, you're like, okay, okay, it's 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 because you backloaded the possible failure, you know, the failure mode or the sort of test of the idea. You spend all your time kind of planning and architecting this brilliant, beautiful thing. And 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. And that sort of iterative thing about testing the riskiest assumption is maybe important, it seems like. For you, did you make that mistake of kind of like overanalyzing, overplanning at the beginning, like not testing with customers?

Less at 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. But like, it was something for me.

This confused everyone else, right?

Right, because they'd be like, well, you're, well, not, you know, what are you doing without having a job? And I'm like, I'm building a book website. And they'd be like, are you going to compete with Amazon? No. Like, are you going to 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, it's like a whole confusing thing. But the beginning, it was just, I like, when I would go visit a friend's apartment, I'd always like be drawn to their bookshelf. You want to see what's on their bookshelf. Anyway, so he was like, okay, what if I can get all these 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? 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 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 animation when you shove the book. So you, right, and then you'd like learn about CSS animation, whatever it is.

So you started building stuff for yourself. Did you ever switch gears to, okay, now I'm going to do the startup startup, I'm going to 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 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 just like not how a person, you know, think like a computer. And once you have that, everything gets easier. But like, why are we typing on computers? And so I kind of got on this like, if we could make our programming environments better, 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 fourteen-year-old who's had a charmed life, and like they just don't know that much, and so like what are they going to write about? And so my version of that is like, look, if there is something personally meaningful, like by all means go for it. That's top ranked, totally. But like second best is like find someone else with the problem and deeply, deeply understand them. I think there's 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 doing that, right? But I can tell you a story about Vanta where Vanta fits that, and it does, 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 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. What was the insight for that?

The insight was I 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 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. Um, but wait, why security? Because like, you know, when I'm talking, I've been talking to you for, I don't know, twenty minutes now. You don't strike me as somebody who's like, I wake up every morning and I was thinking about security during that year off. 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 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. Through Vanta, I 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 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, eighteen 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 or the dots for me. So you took the year or multiple years off to teach yourself.

Two years, yeah.

But then you go to Dropbox, yeah. So you go back to getting a job, yeah. So I feel like we, like there's a part of the story that's like, I iterate, finally I found it. No, no, no, finally you found a job at Dropbox.

Yeah, because 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 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, 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 worked on should be a startup, right?

So what was that story you told yourself? So you spent the two years, you bet on yourself, yep, which sounds amazing. That's a great T-shirt, bet on yourself. But the reality of it, I did it for, 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 had to tell myself certain stories in order to either keep going or to like just maintain a sense of confidence beyond that because the evidence was telling me, yeah, and I just couldn't tell myself you suck because then I definitely suck, yeah. 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 going to, like what's your next goal? What are you going to 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 I should keep going, but my past self sometimes thinks current self should stop, right? And so I was actually like looking at those answers and being like, two months ago I said I should stop. If I got to the point I'm at now, I don't actually think I have counterveiling evidence. I just have stubbornness. Shoot, I should probably stop.

And so that's how you were stopping those projects. Um, 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, 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 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 up. And so for me, for years, it was like, 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 you know, it's like running for me, but like whatever for someone else. And it's like whatever that thing is, do not give it up. And I don't care how busy you get, but sort of know what makes you feel like you and don't drop those things.

Know what things make you feel like you, which is kind of like what you're talking about is habits and hobbies. Is that more of what you're thinking about? Just like that feeling where you like, 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?

Yeah, because I was looking, you read like, I don't know, like 30, 50 books a year or something.

How do you do that? When I was running a company, and by the way, mine was not a 2.4 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 and read the whole book on the bus ride.

You bus to work?

You know, people are like obsessed with cold plunges. 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...

5-Hour is great. I used to take the 38, and 38 is like an actual zoo. It's like anything can happen.

Okay, so, um, so being 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 centered with it. What about manage your own psychology when it comes to self-doubt, when it comes to getting down on yourself? Because I spent two years, I didn't really land where I wanted to land with it. Did you have a conversation with yourself there or a story you told yourself in order to...

Did you just say the BATNA?

Do you use negotiation terms like that just regularly?

No, I like that. And, um, 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 2x evaluation. It just creates this extra aura.

Why? Oh, 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?

That doesn't sound like a great business.