I failed 22 times... then I built a $2.5B Company
Bad Art, Big Bets, and Vanta's Billion-Dollar Journey - November 6, 2024 (5 months ago) • 47:39
Transcript:
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Christina Cacioppo | Uptime, my email is **[email protected]**. It was like the right side, that **usv.com** is way more powerful than the left side. And now you're giving that up. So what are you...? | |
Shaan Puri | You're betting on the left side.
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Christina Cacioppo | You're betting on the left side. Why would you do that? What do you think will happen here?
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Shaan Puri | Do you know what you, Katy Perry, and Serena Williams have in common?
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Christina Cacioppo | I've got nothing.
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Shaan Puri | You're all on Forbes' Self-Made Women list.
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Christina Cacioppo | I hate that list. I hate that list.
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Shaan Puri | And you are ahead of them. Is that kind of amazing? I would...
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Christina Cacioppo | Yes, I would have preferred that list never existed.
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Shaan Puri | You have that Midwest modesty.
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Christina Cacioppo | Yes, nothing good will come from that list.
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Shaan Puri | Yeah, those lists are sort of made for the wrong type of people.
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Christina Cacioppo | Yes, or jail time later or something. Trevor, don't laugh at me. I was never on 30 Under 30, and I'm deeply glad about that now. | |
Shaan Puri | Yeah, that turned out to be an anti-signal. You know, when I was thinking about this episode, the way I think about it is like this: where you are today is where a lot of people want to be. You have a company that's working, it's got a cool startup name, and it's got a cool office in San Francisco. The last valuation, I believe, was $2,450,000,000, but who's counting?
Today, you're at a place where a lot of people want to be. But if we rewind the tape to 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 are: 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 don't take the leap.
You took the leap, and it's not like it hit right away. You created Vanta, and you built this, you know, multibillion-dollar company right off the bat. You did like 35 things wrong or 35 projects that went nowhere. I love that because I spent 8 years of my life banging my head against the wall with failure after failure after failure, each time believing, "This is the time."
You know, let's start where you have a good job.
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Christina Cacioppo | Yeah. | |
Shaan Puri | You have the job at USB, which I think you kind of hustled your way into.
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Christina Cacioppo | I would say I stumbled and hustled.
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Shaan Puri | Okay.
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Christina Cacioppo | It didn't like to stumble hustle. They announced 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."
So, I literally sent them three links to my web presence. I didn't email anyone who knew them. It turned out I knew people from school who knew them, but I didn't pull any strings. I just sent them the links and put them in a form. I was like, "Well, now I’ll go back to making slides."
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Shaan Puri | What kind of links?
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Christina Cacioppo | It was Twitter, Flickr, through the era of this. I had started a design blog a couple of months before, and I lived in Berlin because I wanted to be like a designer who lives in Berlin. Those people seemed to have design blogs, so I started one, and that was it. And they hired me.
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Shaan Puri | Isn't that crazy? 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?
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Christina Cacioppo | Kind of. It was actually when I was leaving, so this was the 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'm sort of like, "But I don't think I like it."
And again, what's going on? One of my hang-ups was, 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 GPU is no longer a benchmark, but he had this illustrious Silicon Valley career—like LinkedIn, Facebook, Benchmark. You know, and you're like, "Me versus Matt Kohler? Everyone will choose Matt Kohler 100 out of 100 times."
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Shaan Puri | Which is, let's say, maybe a part of partially imposter syndrome, but also maybe hyper-logical.
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Christina Cacioppo | I think, like, yeah, but also true. Anyway, I basically said that to Fred, and he said two things, which were deeply insightful.
One was, "Well, you know, Christina, you've gotta get over that." You can either get over that by sort of out-hustling people and using the "fake it till you make it" strategy. He said, "Look, I've seen you in the office for two years. I've worked with you for two years. You're not going to be consistent, so you probably shouldn't try that."
The other strategy is to pick something, go deep in it, and be the expert where no one else is. He recommended that in the fall of 2012, I choose crypto. Really good advice on a bunch of dimensions, right? I didn't take it, but...
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Shaan Puri | Because you didn't believe in crypto, or you were just like, "That's not me."
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Christina Cacioppo | 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 it has all these great attributes, like everyone else wants to be a VC, but like...
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Shaan Puri | I want to.
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Christina Cacioppo | Go make things.
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Shaan Puri | So, you decided to go make things. Take me back to that decision. Was that easy?
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Christina Cacioppo | No, I'm so angsty.
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Shaan Puri | Was everybody patting you on the back and saying, "You're gonna make this happen?" | |
Christina Cacioppo | Totally not what I did. My plan was to save my bonus from the prior year. It was kind of like a finance bonus, and I was going to live off of that as long as I could. So, no job but a bunch of structure. I wanted to learn to code and learn to make products, hoping something would come out of that.
It was 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. Yes, I wanted to start a startup, but I had seen over the two years at USC so many people start startups just to start them. Then they would get into them and be like, "I don't want to work on this," but now I have people in the office and investors, so I can't stop.
I think there was a perception that people took that conservatism as, "Oh, you shouldn't be doing this." Specifically, there was a lot of questioning, like, "Why does no one leave USV who has the option of staying? Why would you do that? 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? Clearly, you don't know what you want to do."
Then there was some tougher stuff. I think one person in particular, who I had been close to, was very focused on the left side and the right side of your email address. At the time, my email was [email protected], and it was like the right side, that usv.com, is way more powerful than the left side. Now you're giving that up. So, what are you doing?
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Shaan Puri | You're betting on the left side.
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Christina Cacioppo | You're betting on the left side. Why would you do that? What do you think will happen here?
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Shaan Puri | So, you have the good job.
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Christina Cacioppo | Yep. | |
Shaan Puri | 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.
Your plan is not even to go start a company; it's to learn how to code. You're going to teach yourself how to code by going online and learning that way. My understanding is that it worked because I went to your website. You have this list of projects.
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Christina Cacioppo | You're like... | |
Shaan Puri | I built all these things.
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Christina Cacioppo | Yeah, none of which you've heard of.
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Shaan Puri | 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, learn this magic superpower, and I'm gonna train in the mountains where nobody's looking. Then I'm gonna come back stronger. Yep, it may not have felt that way at the time.
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Christina Cacioppo | But it, like, I kinda knew I was supposed to feel that way. Then, day to day, there was some amount of like, I spent more than my daily cash allowance, you know? But I kinda knew that's what a better version of me would feel.
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 in New York and opened up this big space in New York that was actually right across the street from the USV office.
So, I got up every day, I got dressed for my job, and I basically walked to the same place, but I went in a different door. Then, I sat with those engineers and they actually...
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Shaan Puri | Dressing up, by the way, is important because I feel like there's something psychological about actually dressing up as if you're going somewhere.
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Christina Cacioppo | I mean, I dressed for tech, but it was like I did not wear pajamas.
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Shaan Puri | Right, right. | |
Christina Cacioppo | Like, yeah, yeah. Then I would go and show up in the morning. I'd do my Udacity tutorial or try to understand JavaScript to varying degrees. Then I would go home at around 6 PM or 7 PM and often keep doing stuff.
Basically, it was like tricking myself into acting like I had a job. I got up every day and was there by 9, but you know, I was just doing the same thing.
I do remember there was a time my family took a vacation that I went along with in January. I came back tan, and everyone was like, "Where were you last week?" Basically, they were asking why I wasn't at work and why I was tan. I would be like, "I'll complain for this," but you're like, "I'll be shocked. Everything is PTO to me."
But it was also like, "Oh yeah, I got this." That was kind of a fun moment too.
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Shaan Puri | 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. It takes 2 minutes, even though in real life, it's 2 years.
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." This is from a book called *The Art of Fear*. Can you... I love that. Can you explain that?
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Christina Cacioppo | Yeah, I think it's deeply true of creative projects. Startups, businesses, and even internet art are all creative projects.
One thing I learned at USV was seeing people complain, but then hearing the stories behind their big successes—like Tumblr, Twitter, Foursquare, and all the big successes of that era. When I walked into USV, I felt like everyone was Mark Zuckerberg. Not actually, but you know, startup founders are people who have an idea, are visionary, and they go into their room and build it. Everyone uses it, and it's like the first or second thing they've done.
Take Facebook, for example. That was kind of all of Mark's projects. So, that's the way it goes. And I'm kind of like, "Shoot, it's never worked for me." So, I'm probably not one of them.
USV was just so helpful in debunking that notion and being like, "Look, a very small number of people can do that, and that's incredible. I wish I were them." But most people actually try a bunch of stuff, and eventually, something might work. It could be the fifth thing or the fifty-fifth thing, but no one really talks about that because it's painful and not fun.
It's supposed to be romantic, but it actually just kind of sucks. I was hungry for two years—literally and metaphorically. It's so much nicer to get praise for being the brilliant person, right? And that's the expectation too. I think I just had a realization that this discourages so many people from starting.
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Shaan Puri | 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."
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Christina Cacioppo | Yeah. | |
Shaan Puri | I will bump into a stranger. Our papers will fall on the floor.
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Christina Cacioppo | Who'll swap?
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Shaan Puri | A paper... a paper. He'll have to come find me, exactly. But then, I'm not into him, but he just pursues me anyway.
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Christina Cacioppo | And then. | |
Shaan Puri | 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.
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Christina Cacioppo | So, you vary that. | |
Shaan Puri | You know, if you watch *The Social Network*, you're like, "That's just how it is." A brilliant genius has a vision, does it, takes off, and then he rides that bull, you know, at the rodeo.
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Sam Parr | Alright, so when I ran my company, The Hustle, I think we had something like 2,000,000 subscribers. We made money through advertising, but we didn't actually make that much money per person reading the newsletter because advertising, in general, is kind of a crappy business model.
I remember sitting down and thinking, "What are all the different ways that I can make money off The Hustle that aren't advertising?" To make sure that you don't make this mistake, Sean, me and the HubSpot team went and looked at a bunch of different ways to monetize your business. We put it all together in a really cool document where we lay it all out along with our research.
We call it, very appropriately, "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.
Now, back to the episode.
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Shaan Puri | We actually, after I read this quote to my team, started using this phrase. It's called **"bad art."** | |
Christina Cacioppo | mhmm | |
Shaan Puri | So, I'll hit up my team in the morning. I'll say, "Hey, let's make some bad art," like intentionally just to almost lower the stakes instead of saying, "Yep, we have to find the next big winner idea."
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Christina Cacioppo | Right. | |
Shaan Puri | Let's just make some bad art today.
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Christina Cacioppo | Yep. | |
Shaan Puri | And the analogy I gave was this: Imagine you go to a hotel or a motel. You're doing something, going to a place that you've never been before—maybe nobody's been there before.
When you turn on the tap, it's like muddy water at the beginning. Yep. If you look at that and you're mortified by it, it's disgusting. You'd turn it off right away and be like, "Ew, bad!" and 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—you can get it out of your system. Then suddenly, the water starts running clean.
I think that framework is very useful for anyone who's doing either creative endeavors or startups, which are a pretty creative endeavor too.
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Christina Cacioppo | Do you know the story about making pots? No? It's from the same book. I think it was around the chapter where that quote was.
Anyway, it was an art teacher who said, "Okay, art school pottery class, you have one assignment all semester. You have 5 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."
Student 1 spends all semester crafting the perfect pot and hands it in at the end. Meanwhile, Student 2 makes 2 pots a day, and they're all back for a long time, right? But over the course of the semester, they hand in whatever, like 300 pots. So, who gets a better grade?
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Shaan Puri | Of course, the 300 pots.
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Christina Cacioppo | Right, yeah. But it's like that concept... yeah, it's so true.
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Shaan Puri | And you have to live it almost to really internalize it.
Actually, a great thing I did once with my company is the marshmallow test, which is a psychological test with kids. It makes a good exercise.
You break your team into groups of maybe 4 or 5, and they get supplies like sticks of spaghetti, 1 marshmallow, a piece of string, and maybe 2 other things like a piece of tape. The idea is, "Hey, you have an hour. At the end of the hour, I will come around and measure whoever from the tabletop has the highest marshmallow." So, whoever can build the biggest tower wins.
What most people do, and what my team did, is they immediately go into the way we do most things in corporate life. It’s kind of like, "Okay, you're in charge. You do that." There’s a sort of segregation of duties. You start trying to plan, sketch a little bit, and then you begin building the tower.
At the very end, you're like, "Okay, okay, it's almost time," and you put the marshmallow on. The entire thing collapses because even though a marshmallow looks so small and light compared to spaghetti sticks, it's way too heavy. You don't realize that because you didn't backload the possible failure. You spend all your time planning and architecting this brilliant, beautiful thing.
The cool thing 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 immediately. They realize, "Oh, it's too heavy. You have to have like 5 spaghetti sticks to hold this thing up." They figure that out right away; they don’t save that to the end to try to perfect it.
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Christina Cacioppo | Yep. | |
Shaan Puri | And that sort of iterative thing about testing the riskiest assumption.
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Christina Cacioppo | Yep. | |
Shaan Puri | Is this maybe important? It seems like for you, did you make that mistake of kind of overanalyzing and overplanning at the beginning, like not testing with customers?
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Christina Cacioppo | Less at the very beginning, because at the start, I was just Bill. 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.
It was something for me, but this confused everyone else. 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." Then they'd ask, "Are you gonna compete with Amazon?" No. "Are you gonna compete with Goodreads?" And I'm like, "Well, you know, with my friends, but like no."
Then they'd say, "Well, what would you say you're doing?" And I'm like, "Mostly battling JavaScript errors, trying to get things done, and spending a lot of time on Stack Overflow."
Anyway, this was a whole confusing thing. In the beginning, I liked visiting a friend's apartment and being drawn to their bookshelf. I wanted to see what was on their bookshelf. So I thought, "What if I can get everybody's books online?" But it was clear that this was not a business.
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Shaan Puri | Right. | |
Christina Cacioppo | Best case, I'm making like $50 a month, you know, from Amazon referral fees. That's not really a business.
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Shaan Puri | But you did it anyway. Why?
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Christina Cacioppo | Because I wanted it. I wanted it, and it was good. It wasn't, you know, like when you do those initial coding tutorials and you're making whatever the other person wants to make, which is not what you want to make. I actually wanted this thing, and it forced me to be like, "Oh, you know, now I want an animation when you shelve the book." So, right? Then you'd learn about CSS animations, whatever it is.
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Shaan Puri | And so, you started building stuff for yourself. Yep. Did you ever switch gears to, "Okay, now I'm gonna do the startup"? I'm gonna do the thing that might actually...
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Christina Cacioppo | Yes. | |
Shaan Puri | You know, get me out of poverty... like self-induced poverty, basically.
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Christina Cacioppo | So at that point, I was very much like, "Look, I just taught myself how to code." Am I that good? No. But learning how to do some of this is much harder than it should be. A lot of it is because our programming tools make us hold everything in our heads. You have to teach yourself to think like a computer and read through code, which is not how a person typically thinks.
Once you have that mindset, everything gets easier. But why are we typing on computers? I kind of got on this idea that if we could make our programming environments better, they would make more sense, and more people would learn to code. So, I was really into that personal problem. Also, you know, living in the future and building back... whatever, all the startup trope advice.
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Shaan Puri | I'm curious about that. What startup trope advice actually helped you?
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Christina Cacioppo | I think the "build something you want" concept is a bit of a red herring. It works in some cases, but you're also very limited by your experience.
It's kind of like when they tell writers to "write what you know." For example, consider a 14-year-old who's had a charmed life; they just don't know that much. So, what are they going to write about?
My version of that is: if there is something personally meaningful, by all means, go for it.
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Shaan Puri | That's top ranked.
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Christina Cacioppo | Totally! But like, the second best is to find someone else with the problem and deeply, deeply understand them. I think there's a variety... Shut your eyes and imagine the future. What's it look like? Build that.
I think this makes sense in retrospect. However, I think in the moment, it's pretty hard to generate reasonable startup ideas doing that.
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Shaan Puri | Right. | |
Christina Cacioppo | But I can tell you a story about Vanta, where Vanta fits that. Yeah, and it does, but it's...
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Shaan Puri | But that's in retrospect. Yeah, 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. Yep, what was the insight for that?
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Christina Cacioppo | The insight was that I wanted to start a security company focused on serving startups. There seemed to be a huge market for security, but no one was really targeting startups. Startups didn't use security tools, and I was sort of like, "Why?"
When does this market go from a $0 total addressable market (TAM) to a $90 quadrillion market size in precise terms?
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Shaan Puri | Yeah, that's the official number.
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Christina Cacioppo | Yeah, exactly. | |
Shaan Puri | But wait, why security? Because, like, you know, when I've been talking to you for, I don't know, 20 minutes now, you don't strike me as somebody who wakes up every morning thinking about security. During that year off, why did you even think about security to begin with?
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Christina Cacioppo | It seemed really interesting. It felt like this kind of competitive cat-and-mouse game with attackers, where there's a real dashboard.
I think one of the things I've... I mean, I guess I knew, but I didn't really know, is that I'm very competitive. I should have played more sports as a kid. I didn't, but through Vanta, I have an outlet for a lot of that energy, which is great.
Honestly, when I was at Dropbox, I worked with this product security team. They were great—super fun and really good educators. It's not like they hosted seminars on things; they just wanted you to fix something. They'd come over, sit next to you, and explain why it was important and how to do it. Anyway, they were just great.
So, in coming up with startup ideas, there was a bit of, "Well, this actually seems like a deep enough, interesting enough space that if I work in it for years, there will be lots of things to explore." 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, it could have been worse.
Right? You kind of look back and think, "Okay, worst case, nothing comes out of this, but I'll feel as good as I will."
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Shaan Puri | Or, well, what are the thoughts for me? So, you took the year, or multiple years, off to teach yourself... two years?
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Christina Cacioppo | Yeah. | |
Shaan Puri | But then you go to Dropbox.
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Christina Cacioppo | Yeah, so you... | |
Shaan Puri | Go back to getting a job.
Yeah, so I feel like there's a part of the story that's like I iterated and iterated, and finally, I found it. No, no, no. Finally, you found a job at Dropbox.
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Christina Cacioppo | 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 or with people. Also, my friends are kind of getting promoted, and it's unclear if I'm employable. This seems bad, and I was really frustrated.
Because again, I wouldn't tell people I wanted a startup to come out of that, but I did. At the same time, I was like, "Well, nothing I worked on should be a startup," right? So, yeah.
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Shaan Puri | So, what was that story you told yourself? You spent the two years... you bet on yourself. Yep, which sounds amazing. That's a great t-shirt: "Bet on Yourself."
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Christina Cacioppo | Yeah. | |
Shaan Puri | But the reality of it is, I did it for... I told you I did it for 8 years. Yeah, and I was delusional enough to keep going.
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Christina Cacioppo | Yeah. | |
Shaan Puri | But also, objectively, it was bad. I had to tell myself certain stories in order to either, A, keep going, or to just maintain a sense of confidence.
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Christina Cacioppo | Yeah. | |
Shaan Puri | Beyond that, because the evidence was telling me, "You suck."
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Christina Cacioppo | Yeah, yeah. | |
Shaan Puri | And I just couldn't tell myself, "You suck," because then I definitely suck.
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Christina Cacioppo | Yeah. | |
Shaan Puri | What were you saying when the evidence kind of said, "You suck"?
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Christina Cacioppo | This is very silly. I had this survey I would fill out, a Google Form I'd complete for myself every Sunday or every weekend.
What are you working on? How do you feel about it? What is your next goal? What are you going to do to move forward?
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Shaan Puri | You made that for yourself.
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Christina Cacioppo | I made it for myself; it was like a personal accountability thing, right? I asked a bunch of questions, and 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?"
Turns out, my present self always thinks I should keep going, but my past self sometimes thinks my current self should stop. I was actually looking at those answers and being like, "Two months ago, I should have said I should stop if I got to the point I'm at now."
I don't actually think I have countervailing evidence; I just have stubbornness. Shoot, I should probably stop.
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Shaan Puri | And so, that's how you were stopping those projects.
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Christina Cacioppo | Yeah. | |
Shaan Puri | You know, when I sent you some questions ahead of this to try to understand what you think is important to talk about, what 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?
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Christina Cacioppo | It's, I think, hard to do and hard to teach. What I try to tell people is to figure out what is personal—not personal sensitive, but personal specific to you. Figure out what makes you happy or centered, whatever those things are, and do not give them up.
For me, for years, it was running 3 or 4 times a week. Exercise, sure, but it was actually just the mind-clearing, cathartic, kind of meditative aspect of running. It was running for me, but whatever that is for someone else, it's important.
Whatever that thing is, do not give it up. I don't care how busy you get, but know what makes you feel like you and don't drop those things.
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Shaan Puri | Know what things make you feel like you, which is kind of like what you're talking about. Is that more of what you're thinking about—habits and hobbies?
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Christina Cacioppo | Or just like that feeling where you're moving through the world and you 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?
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Shaan Puri | So, for you, running is one. What else?
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Christina Cacioppo | 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? So, if I think of hobbies or anything I've done throughout my life, reading is actually one of the biggest through lines.
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Shaan Puri | Right.
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Christina Cacioppo | And so, there's a part of that that just feels like me.
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Shaan Puri | Yeah, because I was looking. You read like, I don't know, 30 to 50 books a year or...?
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Christina Cacioppo | Something... but 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.
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Shaan Puri | I feel like that when I was running a company—and by the way, mine was not a $2,450,000,000 company—I was like, "I have no time to read! Are you kidding me? There are problems everywhere. I'm drowning in problems."
Did you just replace TV with reading or something as simple as that?
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Christina Cacioppo | Yeah, like actually.
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Shaan Puri | Eric told me that you are extremely quick with reading. He's like, "She would take a bus to work."
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Christina Cacioppo | Yeah, and read the bus. | |
Shaan Puri | And I read the whole book, yeah, on the bus ride.
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Christina Cacioppo | Oh, but yeah, I mean over the course of a week or so. But yeah, like actually to stay... I | |
Shaan Puri | Was just gonna take more legendary. He was like...
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Christina Cacioppo | Nah. | |
Shaan Puri | To and from, cover to cover. | |
Christina Cacioppo | No, that was it.
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Shaan Puri | I'm gonna make sure that.
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Christina Cacioppo | I actually still take a bus to work, part of it, so I can just sit there and... | |
Shaan Puri | You bus to work.
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Christina Cacioppo | Yeah, because look, if I take a car, I'm just going to sit in the back with my laptop writing emails. You know, in a bus, like the San Francisco bus, I'm pulling out my laptop on that unless something's really gone wrong. It just forces me to sit there and have 20 minutes between home and work. I like that. | |
Shaan Puri | It's almost much more... you know how people are obsessed with cold plunges?
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Christina Cacioppo | Yes, I.
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Shaan Puri | I think the more hardcore version is to take a San Francisco bus to work. It's like, "Oh, you can endure an 18-minute bus ride with..." | |
Christina Cacioppo | The buses aren't bad. 5R used to be my bus. 5R is great. | |
Shaan Puri | I used to take the 38, and the 38 is like an actual zoo. It's like anything can happen.
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Christina Cacioppo | Yeah, yeah, yeah. No, 5R is a great bus. I miss it. I miss it. | |
Shaan Puri | Okay, so Benjieren psychology said to figure out what makes you feel like your most authentic self and make sure you stick with those things. Keep doing those things; it'll kind of keep you centered.
What about Benjieren psychology when it comes to self-doubt? When it comes to getting down on yourself? Because I spent two years and I didn't really land where I wanted to with it. Did you have a conversation with yourself there or a story you told yourself in order to...? | |
Christina Cacioppo | Yeah, I was so annoyed. In retrospect, I was being so pretentious. Life was good, you know? Again, like the BATNA [Best Alternative to a Negotiated Agreement], my worst-case outcome was becoming a product manager at Dropbox, at the height of Dropbox's power. My life was great. | |
Shaan Puri | Did you just say "the BATNA"?
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Christina Cacioppo | 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.
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Shaan Puri | Do you use negotiation terms like that just regularly?
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Christina Cacioppo | Hopefully not. That sounds kind of obnoxious. I'll try not to. No.
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Shaan Puri | No, I like that. I've always felt that if you build a great Silicon Valley company internally, you should be a totally normal person. But outside, you should have that like 10% crazy.
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Christina Cacioppo | Yeah. | |
Shaan Puri | It just gives you like actually a 2x evaluation. It creates this extra aura. Totally true. Wow, she's barefoot all the time. Why? No, interesting. She must be one of those real outlier types.
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Christina Cacioppo | Oh my gosh!
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Shaan Puri | Alright, when I asked you about this list of ideas that you did, I looked back on my career. Even when I went through eras where I tried something and it didn't work, a lot of the time I look back with the benefit of hindsight now and think, "Oh, I was just sort of an idiot about it." Had I actually either stuck with it, 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?
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Christina Cacioppo | Like they're art projects, and I say that with deep love, but like, they're not businesses.
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Shaan Puri | Okay, the voice assistant for biologists? Yeah, that doesn't sound like a great business.
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Christina Cacioppo | That was just comically bad. No, yeah, there was a deep lack of any commercials in nearly everything on that list. I think that's part of why Vanta has had commercials baked in from the very beginning, because I made that mistake.
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Shaan Puri | You learned your lesson.
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Christina Cacioppo | So many times.
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Shaan Puri | What about now? If you weren't doing this, or in general, when you operate a business, you see a bunch of pain points, blind spots, and maybe parts of the market that are unaddressed.
If somebody's listening to this right now and they are looking for inspiration or ideas that spark thoughts in their head about stuff they could go do, where would you look? What would you recommend people think about? What problems do you think need solving?
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Christina Cacioppo | Yeah, I think so. So much of what I think about that's not directly in my wheelhouse is something around running a B2B SaaS or being in a B2B SaaS business. Forget running it, just being in it.
There's like... someone please fix the go-to-market tooling stack. There are 9,000 tools, and none of them work well together. It's like you jerry-rig them together in this Rube Goldberg machine, and the marbles are all over the floor. If anyone wants to tackle B2B SaaS, just fix that! Go full stack on all that.
But for people who don't want B2B SaaS, which there are hopefully many, I think the cross-advantage came out of... I mean, I liked it going in, but now, of course, I really like it.
That was about picking something you want to learn about and just going to talk to anyone you can about what their days are like, what their problems are like, just like what's going on. Try to develop a mental model of this space.
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Shaan Puri | The story I heard about Vanta, which sometimes we make up for a prospect story, so I don't know... you tell me. Can I?
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Christina Cacioppo | Try to actually tell the true one.
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Shaan Puri | Like, blink twice if it's true... and yeah, whatever. But you were at Dropbox, working on this thing called Paper. I remember seeing Paper at the time; it was this idea of a collaboration tool.
You go to launch Google Docs, and Dropbox is like Google Docs. You go to launch it, and it's like, "Hey, we don't have SOC 2, so we can't really launch, or customers can't use it." And you were like, "SOC what?" | |
Christina Cacioppo | Yep. | |
Shaan Puri | And you didn't really know what that was. You were like, "So how do we get that?" You started asking questions to try to understand, "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.
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Christina Cacioppo | Yep. | |
Shaan Puri | And the next part of the story that I liked was, even though you had just spent two years learning to code and built 35 projects, coded them up, and shipped them out, you didn't write code for this. You were like, "I'm gonna test this idea with an Excel spreadsheet only."
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Christina Cacioppo | Yep. | |
Shaan Puri | And you went to one or two startups, I think Y Combinator (YC) startups, that you thought might need this. You were like, "Hey, if I did this for you, would that be valuable?" And they're like, "Oh yeah, sure."
How much of that is true?
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Christina Cacioppo | All true. The stylized part is that all the Dropbox stuff happened. There was no light bulb moment; I was not smart enough to have a light bulb go off over my head at the end. I wish it had been that way.
But it was just like I learned about the whole process and learned what it would take. Then I basically ran screaming from the room because it just sounded awful, especially when we were trying to launch and even figure out if we had product-market fit. The idea of going two years of work to then see if we have product-market fit was like, "Bad, bad!"
How do I find reality faster? I came back to it later, did the spreadsheet thing, and I think honestly it's because there are sort of five things on the list. It's kind of at the point where you're like, "Okay, I can write somewhat shoddy JavaScript, but 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? So, how much of the validation can you front-load there?
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Shaan Puri | So, I think a lot of people hear that and they're like, "You should talk to customers. You should validate if people want this. Make something people want."
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Christina Cacioppo | Yep. | |
Shaan Puri | 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 about it? Who do you talk to?
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Christina Cacioppo | Yeah, what do? | |
Shaan Puri | 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... yeah," or "Maybe I'd be interested." And you're like, "They totally loved it."
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Christina Cacioppo | Yeah, so on the false positives, anything that is not "Can you do this for me now, tomorrow, or next week?" is a no. People are really kind, and they want to be kind, so they rarely say no. Instead, they often say things like, "Oh, maybe next quarter," or "I don't need this, but my friend might." Those are hard no's.
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Shaan Puri | You should date my friend.
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Christina Cacioppo | Nose totally hard nose. I think on who to talk to. I mean, look, we started with anyone who would talk to us, and then it was just like... and then it ended up being coworkers, former coworkers.
Because you had like some... well, I don't know if you know anything about this topic, but you're kind of the nicest person, and so I'll like give you a half an hour, sort of thing, and then just fan out from there.
At the end, when they're like, "Well, you know," you ask them, "Do you have anybody else?" and they list people. And like, say yes, follow up with customized emails. I could forward, you know, like make it easy for them and just keep going out.
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Shaan Puri | Yeah, I think that's an important one. Make it easy for them to do the thing they said they want to do.
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Christina Cacioppo | Oh yeah, like follow up and be like, "Thanks so much for meeting me." I would love to talk to your friend, Eric, who said this. Here's what I'm working on. Just assume they will write them an email and they will forward it.
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Shaan Puri | Exactly. Yeah, so have you ever read this thing called "The Mom Test"?
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Christina Cacioppo | Yes.
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Shaan Puri | Do you subscribe to that?
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Christina Cacioppo | Yeah, generally. | |
Shaan Puri | Yeah, that was helpful to me when it was. 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. Then, at the end, if you want to ask them about your solution, great! But just assume they don't really know what the solution needs to look like.
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Christina Cacioppo | Yeah, I think that's true. Try to avoid yes or no questions, which is harder than it sounds. There are a bunch of user research tips and tricks, like if somebody mispronounces something, go with their pronunciation. Otherwise, they're going to... don't.
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Shaan Puri | Break rapport. | |
Christina Cacioppo | Exactly, exactly like a lot of... | |
Shaan Puri | I think I do that, and it sort of is like a problem because it's kind of a know-it-all move.
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Christina Cacioppo | Right and... | |
Shaan Puri | Then it makes them feel like their mind goes over there. Exactly. "Oh, am I being stupid? Did I say something stupid?" Exactly.
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Christina Cacioppo | Where you just want them to stream of consciousness at you, basically.
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Shaan Puri | 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 explode right away necessarily.
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Christina Cacioppo | Yeah. | |
Shaan Puri | And I've seen your ARR chart, which looks beautiful.
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Christina Cacioppo | Hockey stick. Totally. | |
Shaan Puri | But if you zoom in, it's like, "Wow, that was a year where it's like pretty small." Then it started to accelerate.
Was there anything you did that you felt was interesting or unique that kind of took your creativity over?
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Christina Cacioppo | It's so funny looking back because I sent a bunch of outbound emails to Y Combinator (YC) companies, but I didn't know the word "outbound" at the time. I was emailing YC founders for feedback, and I legitimately did want their feedback.
Kind of to this, it was like half of, "Okay, I'm going to spend 60-70% of the call talking about the problem and how you're solving it," and then in the end be like, "I'm building a thing. Would you like to hear about it?" But it was like totally cold outbound, you know? I just didn't know that word.
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Shaan Puri | So, you emailed a bunch of YC people. That got the ball rolling. What happened after that?
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Christina Cacioppo | Honestly, the early strategy was to just do and try everything, and then see what works.
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Shaan Puri | So, what did work? | |
Christina Cacioppo | The outbound worked. There was a word-of-mouth aspect. We tried really hard in the early days to basically build this call response in founder Slack channels or VC Slack channels.
Where someone said "SOC 2," someone else would say "Vanta," and you just wanted this... you know, "Talk to Vanta."
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Shaan Puri | You're saying, "Build the brand in people's minds."
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Christina Cacioppo | Yeah, and that was great for a while. Then a bunch of knockoffs came, and there are a bunch of other ways to get talked to. So that association...
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Shaan Puri | I remember you guys on the billboard. It was like, "What is it? Compliance that doesn't talk too much?"
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Christina Cacioppo | Yep, still up.
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Shaan Puri | Yeah, that was good.
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Christina Cacioppo | Still up? Yeah, I joke with people that we make software, but we also make a billboard, and we're equally known for both. So we're like equally as important.
What else? Podcast advertising really worked in... I mean, actually, it still really works, but it really worked in the early days. I thought podcast advertising was just going to be like sending money out the window. I was totally wrong. | |
Shaan Puri | And that's what happened. Somebody on your team pictures you, this Eric, pictures you.
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Christina Cacioppo | Eric was like, "I want us to get $20K to go on 'This Week in Startups' or something." I rolled my eyes and said, "Fine, whatever, go." She was totally right. | |
Shaan Puri | Eric is like this mythical figure to me now, where I've only ever heard great Eric stories. So, I don't want to hear any bad Eric stories or ideas you had that didn't turn out. Please, don't tell me.
Alright, I want to ask you about a couple of your controversial or maybe just less consensus opinions. I've seen you write these somewhere on the internet. You tell me if you still believe these and why.
**Consistency is overrated.** This is on your website.
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Christina Cacioppo | Oh yeah, people read a lot into this. I'm just joking with myself because I say, "Contact me through these four ways," that are all in totally different names on them.
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Shaan Puri | Oh yeah, so like it's just minor naming consistency.
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Christina Cacioppo | Is overrated, just like minor self-awareness. I think people believe it's meant to be a broad philosophical statement. Do I actually think it's a broad philosophical statement? No, probably not. I think Vanta has taught me that consistency is actually underrated.
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Shaan Puri | Yeah, I was gonna say you strike me as somebody who's **consistency first**.
Yeah, it's bad when the goal posts move. I don't know if you're saying you think this or that other people do.
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Christina Cacioppo | I think this... People, the advice tends to be right. Like, you know, if your goal posts keep moving, it's hard to find happiness. You're always chasing something, that means... | |
Shaan Puri | So, like, what does that even mean? The goal?
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Christina Cacioppo | Post moving, like, I think... I mean, it gets bought in lots of forms of life. But 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 the seed round, you want to get to like $1,000,000 in ARR. But then, by the time you get there, you're like, "Actually, I want to get to $10 million," right?
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Shaan Puri | That's it.
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Christina Cacioppo | And there's always something you are chasing. 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 that you thought was great. Why can't you think it's great?
I think that can be true in some cases, but I actually think the trick—or downside—is if you're only happy when you hit a goal post and then you're moving them, you'll never be happy if you actually just like the work.
It doesn't matter. I think a lot of things are more sustainable when you like the work, especially when you have a lot of work to do.
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Shaan Puri | My formula is **progress equals happiness**. This means that no matter where you are—sort of like the y-intercept doesn't matter—the slope matters.
So, wherever you're at, if you don't feel a sense of progress in your life, you will feel unhappy. Then, you'll feel even worse; you'll feel guilty for feeling unhappy.
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Christina Cacioppo | Yeah. | |
Shaan Puri | 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.
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Christina Cacioppo | Right, right. | |
Shaan Puri | 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 and that you care about.
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Christina Cacioppo | Yep. | |
Shaan Puri | And I think that in that sense, moving the goal post is great because you're saying, "I would like to continue making progress." I enjoy progress so much; why would I stop? My progress stops my happiness, right? It's a different way of looking at it.
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Christina Cacioppo | Do you remember a deep cut from 10 to 12 years ago? Jess, who is the founder of Polyvore at the time, now at Sequoia, wrote a blog post about founder psychology.
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Shaan Puri | No, what did it say?
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Christina Cacioppo | It was like, "Why are founders always unhappy?" And she's like, "Especially when their companies go like this," [gesturing to a line going up into the right].
She's like, "Because if you zoom, you know, again, the Y-axis is getting higher. What is this?" Because if you zoom in on the graph, it doesn't look like a 45-degree angle. It looks like a roller coaster that is going slightly higher.
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Shaan Puri | Right.
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Christina Cacioppo | Right, but it's like the roller coaster along the way. And like, you know, even when you zoom out and you've got this lovely 45-degree line, the downs hurt every time. | |
Shaan Puri | Yeah, there'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 that high standards are bad. You think that in general, so people don't say this.
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Christina Cacioppo | Yeah. | |
Shaan Puri | But they imply it in different ways. You know, "Don't have such high standards." What is the situation where that's come up for you, or you felt that?
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Christina Cacioppo | I think a lot of Vanta's stuff, both within the company and with partners or folks outside, is important.
Some of the feedback we get that I kind of appreciate more than anything else is that people care. People respond super quickly. You know, again, something might have gone wrong, but the person tries really hard to fix it.
I think those things definitely don't happen everywhere by accident. It's not to say I had, I mean, 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." It's kind of scary. Did I join the right place? What's going on?
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Shaan Puri | What's an example of that? Where would somebody feel that?
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Christina Cacioppo | A couple of places, but I guess in go-to-market, our expectations around quota and attainment are way off industry standards. They're way higher.
I think if one just hears them in a vacuum, they're sort of like, "What is this? Why would I sign up for that?" Then they join, and it's like, "Oh, because you're surrounded by people who are into what they do, getting better every day, and want to get better every day."
That sort of environment can be really infectious.
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Shaan Puri | 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 a few weeks ago?
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Christina Cacioppo | No. | |
Shaan Puri | Do you know what Mr. Beast says? Are you different from...?
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Christina Cacioppo | Like, yeah. | |
Shaan Puri | So, like, right around the same time that Paul Graham put "Founder Mode" out there, I was like, "Oh, Founder Mode." But wait, what is it exactly?
It was like, I think yes, but what part of a lawsuit? Mr. Beast's internal document he wrote for his production team leaked a big part. We've gotten to know him and become, you know, pretty friendly with Jimmy over time.
And it's just like, the number one thing—if you go hang out with Jimmy for a couple of days, you walk away and you're like, "Oh, that's what people mean when they say reality." You know, Steve Jobs used to have this reality distortion field.
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Christina Cacioppo | Yep. | |
Shaan Puri | And it's... literally, his company is based in a tiny town in North Carolina. He gets people to move there, and once you're there, you're in his bubble.
In his bubble, the expectations of what work is about, what success is about, what we're able to do, the timelines we do them on, and what it means when something says "no, not possible" are all different. One of his key philosophies is to "push past the no." He emphasizes that you don't always have to get it to be a yes, but if you come back and say, "Oh, we asked for the permit and they said it's going to take 6 months," he responds, "That can't be the end of the story."
We saw this mindset in action with every little thing. For example, we wanted to play basketball the next day, but it was midnight. Someone said, "Oh man, I can't wait till tomorrow; I just want to play." He replied, "Well, why do we have to wait?"
We said, "It's midnight, Jamie. What are you going to do?" He insisted, "I'm sure there's a gym around here somewhere. Let's go find one."
We argued that the gyms would be locked and schools wouldn't be open. He said, "Call the athletic director." He encouraged us to call all of them right now in the county and offer any of them $1,000 to see if they'll come open it.
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 that everyone else would immediately default to thinking, "This is not possible, not feasible, not going to be doable." Whereas his default assumption on any given thing is, "Why not? Of course, we could do that."
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Christina Cacioppo | Yep. | |
Shaan Puri | It's just a matter of deciding. If we want it, we'll do it. If we don't, we won't. But that's it.
Then you just see that time after time after time. Hanging out with them on big things, like the videos that they're going to shoot, but also the small things.
It's just a different gear. It's like, "Oh, your gear is like my stick shift; mine only goes to 6, yours goes to 9."
Okay, if I'm going to hang out with you, I now need to decide how I'm going to get to 8 or 9. Because otherwise, I'll just be sticking out. This won't be the right place for me.
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Christina Cacioppo | Totally. I think there's... I mean, I think also if you experience that and you're like, "You know what? I'm a go with 6."
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Shaan Puri | Right.
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Christina Cacioppo | Totally reasonable decision. Like, not that you know, arguably maybe a better decision in some cases. It's like totally fine. But there might be a 9 for any given thing. I think it's a helpful mindset.
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Shaan Puri | You also raised a bunch of money late. So, you didn't raise early on. You got to $10,000,000 in ARR before you went and raised your Series A.
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Christina Cacioppo | Yep. | |
Shaan Puri | I'm not so curious about why you did that because I'm guessing the answer is pretty simple, which is that we didn't necessarily need it. We just stayed focused on selling the product that was working. But more so, when you went to go do it, what was that experience like? Because...
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Christina Cacioppo | It was. | |
Shaan Puri | You had leverage.
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Christina Cacioppo | It was great. It was really funny. So, people or VCs in San Francisco, Bradley, like, knew we were doing well because of the Slack channel chatter or like an event that had come up. But they sort of didn't know how well.
And so, there was one pitch meeting I remember they...
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Shaan Puri | And sorry, you kept it low key, right?
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Christina Cacioppo | On purpose, we kept it low-key because we had this great idea, and everyone else thinks they can do it. I wouldn't like to spell out what we're working on, but I think it has potential and requires thinking on your feet. I would rather they not know because then someone might start knocking us off and copying.
Anyway, I met with a very smart VC who is very good at his job. I went in to pitch and started walking through the slides. When I got to the ARR ramp chart, you know, the one at the end, his jaw just dropped. He was clearly speechless, looking at it, and he said, "I thought you were at like 2.5." I replied, "No, that was, you know, the 10."
Anyway, he said to keep going, and at the end, he was sort of like, "We're not going to be able to do this. I can try to introduce you to someone else, but you know, it was fine. There were other people." It was an interesting pitch experience.
Then, I went into a meeting with another VC who is also very good at his job. He said, "You know what? I thought you were at 9.4 because I'd taken your Twitter chart and backed it out." | |
Shaan Puri | I actually did take the points. | |
Christina Cacioppo | The counted the pixels and I was like.
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Shaan Puri | You know, I did the proportions. He was like, "She said 10." So if this is 10, yeah, where was she a year ago? Get 2.7 or whatever.
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Christina Cacioppo | He had basically done that, and that was also... you're like, "Hell, it's great! It's so good at your job. It's so fun!" | |
Shaan Puri | Is that who you end up going with, or no?
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Christina Cacioppo | No. | |
Shaan Puri | You're great, but Sequoia's calling.
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Christina Cacioppo | No, but I think actually it was until the goalpost stuff. I'm, you know, not very good at celebrating, but it was a moment where I took a... I mean, a beat, like a week. I was like, "No, I am gonna tell this story and what we've done." I'm deeply proud of it. I would have told you that, but now I 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. So that was just... then it became like, I still kind of hate fundraising, but it was talking about something I believed in. It's fun, right?
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Shaan Puri | Eric told me that he thinks you're great at negotiating. | |
Christina Cacioppo | You said "funny."
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Shaan Puri | You said that's surprising to you, but he was not wishy-washy about it.
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Christina Cacioppo | It | |
Shaan Puri | 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.
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Christina Cacioppo | Yeah, no, it's really surprising. I think if I'm confident in it, I'm actually confident in it. Then we'll just stand and like not blink, not swerve. If we're playing chicken, I won't eat the marshmallow. It's like, "I got it. Let me know when you want these terms. I'm happy to sit here and wait."
Actually, truly, I'm happy to sit there and wait at that. So I think it's just a lot of that. It's like, if I believe it, I won't flinch.
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Shaan Puri | Cool! Well, thank you for doing this. This has been amazing. Where should people find you and find Vanta? Maybe give it a shout.
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Christina Cacioppo | Yeah, [visit] Vanta.com. If you need any help with anything security or compliance related, we would love to help you out. | |
Shaan Puri | Awesome! Well, thank you for doing this.
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Christina Cacioppo | Thank you so much.
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