Today on Leaders, Christina Cacioppo. Her story is one straight out of a Silicon Valley textbook. After graduating Stanford, Christina began as a venture capitalist funding Jack Dorsey's early Twitter alongside Tumblr, Etsy, and Kickstarter. Then, after her time at the glory days of Dropbox, she set out to build something of her own. She taught herself how to code and turned an Excel spreadsheet into Vanta, a $2.5 billion business. Christina, welcome to the show.
Thank you so much for having me.
Okay, so you once said that you never thought you were going to be the type of person that would be a founder, right? So what's your view? Can anyone be a founder if you can have that view and then become a unicorn founder?
Yeah, I do actually believe that. I think it's... it may or may not, or parts. I think actually, I think the job is so multifaceted that no part comes easy to everyone or really anyone. I think some people are better at making it seem that way. Like some founders are good at that and want to be good at that. But I think the job is so multifaceted that there's a lot of different types of people who can be great at it.
So, the way that you're describing it makes me feel like it's like, you know, if it's a pie with different slices, you're going to be strong at some of those slices and then all the other ones are going to be the gaps. And so the way to become a good founder would be to identify the gaps and fill them in.
That is how I approached it. There is like another strain of maybe even more conventional wisdom which is like kind of screw the gaps and just do what you're great at. And I think again empirically that works for people too. I think for me, doing what I did worked better for me.
Okay. So also part of this would then be know thyself.
Yes, I think that is deeply true. Yes. There's a lot of ways to make it work, but you got to make it work for you.
When I started off in entrepreneurship, I just remember being terrified of leaving my job because it feels like a lot of stress, and I still always reflect on that as maybe the biggest decision I ever made. How do you reflect on that? Was it easy for you?
I think the first time I did it, no, and the second time, yes. And I think some of it's like everything's harder the first time, no matter what it is in life. I think some of it's the California ethos where you're like, 'Ah, you left your job, but like, you know what, the worst thing that happens is you're interviewing back at the same place in two weeks and you don't want that outcome.' But like, aren't you so lucky that that is the worst case? I think the first time I was, I don't know, probably 25, 26. I had this job that was, you know, quote unquote very good. I mean, I liked it. Everyone liked it. People told me, 'Why would you ever leave this job?' And I think some actually what was really hard was people around me with good intention kind of being like, 'Why would you leave this job? What's wrong with you?' And I think that caused me to be like, 'I don't know, is something wrong with me?' Which some of that self-reflection was probably good. I definitely took it too far in retrospect.
Quite interesting like hearing that because these are moments, pivotal moments in someone's life where you're not sure of yourself, right? You're not sure of the path and you have different voices around you basically trying to sometimes do the best for you and sometimes coming from a place of their own regret and their own worldview. And it's interesting that at 25, 26 you still knew what was the right thing for you. What do you think was the insight from that?
I think it was... there was like nothing, no claim to like brilliance or even really self-insight. I think it was just I was in that job that everyone liked and I mean I kind of liked but I didn't want to be in it. And I felt that friction and again I kind of had somewhat grappled with the like, you know, I don't know what is quote unquote wrong with me that I don't want this thing everybody else wants, but I know that is true and I feel that. And so I think there was something to like that tension.
Okay. So you obviously going back to I guess just before this, you're at Stanford. Classic, right? That was just yesterday, of course. Yeah. So you've just freshly graduated from Stanford. What was that like? You know, you hear so many stories about this. Was it pivotal to your entrepreneurial success or just like a stepping stone?
Um, what do I think? I think so. I did four years at Stanford and got a microeconomics degree and very much thought I was going to be a microeconomics professor until the very, very end.
Everyone on Twitter this week. Exactly. Excellent. All right, just dusting that off. Let's just pivot to a tariff lesson then.
Love macro, all witchcraft as far as I'm concerned. But until the very, very end, and the reason I wanted to be a professor was, I mean, I both really liked economics and my parents were professors, and so actually it was like a very comfortable job description and I like understood it. I think in contrast to many people who think it sounds very prestigious, to me it's like what my mom did literally. But anyway, at the very end, I sort of realized that adults could do other things with their lives. And so I did a fifth year at Stanford and got a master's degree, but...
Is that your definition of something else with your life?
Yeah, exactly. Yeah, exactly. Was more education. It's like a strong default. But actually took a bunch of design classes, and so it was product design and somebody was like human-computer interface, and that was so different from doing econ problem sets. So that was really the something different, and then that sort of launched me into like kind of this different world than I thought I would be in. And so that part I think it was actually like that fifth year that was probably in retrospect the most kind of pivotal because it opened up this whole other set of doors.
And where did it take you?
It initially took me to Berlin because I'd never been and spoke no German. But they had this kind of post-school, Dutch Telecom, like German T-Mobile had this like post-school internship program where they would take design students for six or nine months, and I somehow snuck my way in and lived in Berlin and, you know, got paid 500 euro a month, but it was great. And that was when like you could do that in Berlin a bit. You can't really do that of the Berlin of today. But I think one, it was like the work was, you know, design and user interface design and like concept design, and then the people we were interacting with were all designers, and there was like kind of this emerging tech startup scene actually not in Berlin but mostly in London then, and it was just again this whole other world that was like very neat. And from that, I got really lucky, and I was reading the blog of a venture capitalist in New York called Fred Wilson, USV, and a blog post basically went up saying, hey, you know, we've had this great analyst on our team for a couple years, but he's moving on, and so we need a new analyst. So if you're interested in his job, send us links to your web presence. And I read that and was like, what is this? You know, I kind of knew the firm, but you're like, what job application is this? What's a web presence? Who would apply for this? And both like I want to apply, but like what's a web presence kind of. But I'd actually start, you know, I had a Twitter account. I'd started this like design blog in Berlin because I was trying to be like the other designers. And so basically at the 11th hour, right before the form closed, I sent them four links and ended up getting hired off the internet.
Wow. What are the four links? Your Twitter, it was Twitter, my design blog, which was quite bad, but you know, maybe LinkedIn, and that might have been it. Wow. Yeah, that's quite impressive. I mean, 2010 internet. Yeah.
No, there's funny. It was like they actually didn't have another application. And in retrospect, there were people like professors at Stanford who knew the folks at Union Square Ventures. I don't know, I was too dumb to like try to be like, oh, have somebody email. Didn't do any of that. Just sent links off into the void. Which actually gives me a ton of respect for the folks at USV and how they hire. Because literally it was three links. It wasn't, you know, and then the Stanford person emailed someone who emailed someone, didn't do any of that.
Okay, so Fred Wilson hires you. Yep. And Union Square Ventures go on to become one of the most successful VCs around. So, who are some of the people that they backed?
So let's see. At the time, they had backed, you know, Twitter, Tumblr, Etsy, this company called Tenzen, which no one knew of at the time, is now [__] but same company. Foursquare, Coinbase was like basically the first institutional investors, one of the first in Coinbase. The thing at the time, and this was early 2010, so it's large networks of engaged users, which you know I think maybe sounds kind of obvious or like of course you want to invest in like the big successful thing, but at the time, again 15 years ago, it wasn't. It was like lots of people use Twitter, but would the thing ever make any money was deeply unclear. And merges it with an AI company, you know, maybe it's still deeply unclear in a different way. But for the most part, like you know, those business models very much got proved out. But I think again early 2010, if I 2009, 2010 is when Fred on his blog coined the term freemium, which just feels part of the at least tech vernacular.
Yeah. I didn't know that's where it came from actually. Yeah.
Right. But there are just things like that. Now we kind of call it PLG, but like that's what it was. And this was like this time where it felt like things on that part of the internet were so new and all these concepts were being created and there was something there, but we didn't quite know what it was. It didn't have words for it. And anyway, I think freemium's like a neat like case study of that where now we all kind of know what it is and you're like, 'Oh, of course that's a business model. Like is it yours? You choose it. Move on.' But at the time it felt like more you were excavating something new.
So, did you get to work with people like Jack Dorsey?
A little bit. I think there were founders that, you know, were very established and so weren't kind of coming through the office on a regular basis, but a big part of the job or when I joined it was kind of three investment partners and me. And so, I probably met, you know, two or three founders a day for two years straight. And so, just got to meet lots and lots of founders of all different sorts and stripes.
What's a good example? So if I'm a, you know, mural founder building one of these companies and I step into Union Square Ventures office, I'm probably quite excited. I'm probably quite nervous. I turn up, I've got a meeting with you. What are some of the questions that you'd ask me?
Oh my goodness. I think so for me it was funny because like I was, you know, the young kid basically at the firm and no one really wanted to meet with me nor, you know, they wanted to meet with Fred, they wanted Brad, Albert, right, the partners. Which is I think something I struggled with in the beginning because I was like, oh yeah, I understand why you don't want to meet with me, like I'm sorry, not what anyone actually wants to hear. I think what I realized the job of a like kind of young person investment analyst at a firm is not to apologize and not to gatekeep, but to like figure out what that person is working on, how it compares to how the partners think, and then like direct them or route them to the right partner. We talked about Fred in his blog, like lots of people, especially in New York at the time, knew of Fred and everyone wanted to meet with Fred. But if it was like someone working on a developer tools business, they were better served with Albert. If it was someone working with like a new protocol, Brad was the better person, right? And so there was this like router. And so I think a lot of the questions when I actually learned how to do the job, I was sort of this like router and translation layer between the entrepreneur and the partners. And then after that meeting, I'd go to the partner and say, 'Hey, I just met, you know, Paulo, and Paulo is working on this thing and he's gonna explain it this way and you'll think it's that, but it's actually this and go down this,' and like kind of try to matchmake a little bit there. And that's what I think the job actually was like, a translator. And it took me like six or so months to like figure that out, but then once I figured that out, it got a lot better.
Okay. So you actually view your space there in between as someone who you understand what the entrepreneur is working on and you understand what the partners are looking for from a thesis point of view, but sometimes a founder is not amazing at communicating the needs to, yeah, in the way that you know again the partners are wonderful but these like, you know, three guys kind of think about the world and it's around the idiosyncratic way and so it's just yeah, it's like translating between those two. As a founder pitching VCs, you're quite often told to your point, try to get away from the analysts and speak directly to the dealmakers.
I do think it's good advice.
It's good advice. Yeah. But how does that impact you and feeling, you know, do you feel insecure about yourself and your place around that? How does that, you know, how does that impact your career? Or what did you do about it?
Yeah. I think what I did was try to kind of be like, oh, that all makes sense. I wouldn't want to meet with me either. This, you know, poor person unfortunately got stuck with me, like what is the best thing I can do for them? And that's where I kind of figured out that like translation piece.
Got it. Okay. So in general your advice for founders is basically do the same as in you've been in that role so you've been the person who's been overlooked as a result of it. Is it a good career path for people?
I think those who like investing, who really like investing, and I do think, and I saw it at USV, investing done well can be this like really intellectual, really interesting job. I think there are parts of it that are really similar to academia. I think that, you know, outcomes and upside are very different between academia and kind of an investment role. But I think done well, you know, you develop a thesis, you go and research it, you have this wonderful excuse to basically call up anyone you want and they'll be like, 'I'd love to come to your office so you can ask me a million questions,' right? It's this kind of racket, sort of like podcasting, like actually there's like journalism, podcasting, investing. There's a couple of these roles that are really neat, like structured rackets but in a like wonderful way. But I think it is fundamental and the people who are best at it, and again I think USV was excellent at this, I got to go to board meetings and see not everyone I thought was excellent at this, is they're investors, not operators, like they're not running the businesses and they don't see themselves as someone who's running the business. And that's really like that is I think actually a very important distinction. So back to your question, I think it is a like great opportunity for someone who is curious and wants to invest. I think for someone who wants to operate, you should actually just go operate. Like you want to build something, you should just go build the thing.
Yeah. So, you got to meet the founders of like Tumblr, Etsy, Kickstarter. Obviously, Kickstarter is a good one. You know, Jack Dorsey, Brian Armstrong of Coinbase. What are some of these traits that these founders had that you could see a straight line through?
Yeah. I think one of the really helpful things for me was like, even the companies you mentioned, all the founders are really different. And I think that was actually really helpful again sitting there and being like, okay, the media narrative, especially at the time, was like there's one type of person and they probably have been, you know, coding since they should touch a keyboard. And when they launch something, you know, everyone on their college campus immediately uses it cuz they're a genius.
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And that was kind of the narrative. And then you meet just whole swaths of people who are successful and be like, oh, some did that, some did something else, some went to art school and like lived in a brilliant garage for a while. And Kickstarter kind of came out of that. It's not quite the Kickstarter story, but like adjacent. I think the people who were most successful truly liked what they were doing and they liked it because they liked the work, not the like prestige that came with like other people liking their work, if that makes sense. And I, you know, I think those two things are easy to conflate. You see people conflate. I've conflated them at various points in my life. But I think the people who again kept doing it just liked the work. And I do actually think there's so much work you kind of have to like it. There's just too much to not.
Yeah. Okay. And obviously I suppose mission-led in a category as well.
Yeah. And there's, it's, you know, I think sometimes this takes like a moral tone of like, you know, mission-driven founders are good and, you know, mercenary or like even though we call it mercenary, you know, like money-led founders are bad, and I think that's too harsh. But again, I think it does come to like there's so much work before an outcome or to get to an outcome, you kind of got to like the work.
Do you feel like being around those types of people drove you to want to become a founder?
Yes, 100%. Yeah. And again, that was kind of this tension where I'd, again, I got to talk to people all day. I got to have these pitches. It was so cool. And then they'd leave and I'd be like, 'Now I get to write an email about everything I learned.' And it felt so unfulfilling. And I remember saying this to a founder friend who's backed by USV and he was basically like, 'Christina, after I have a meeting, I also go write emails. Like you realize that, right?' And I remember just being like, 'No, but like your emails are different. Like they're more impactful. They matter more.' And he was sort of like, 'You're crazy,' you know, like agree. It was kind of fine. Agree to disagree. But there was again, there was just something there where it felt like sort of unfulfilling to sit on the sidelines and analyze all of the time.
Yeah. So then you launched Vanta and had a runaway success.
Yeah, exactly. Totally, truly an overnight success. No, years in the making.
Excellent. So what did happen in between? There was like six years.
So to that, I think, you know, of founders who came into USV, some could code, some could not, some could kind of build things, build software themselves, some could motivate people to build software. I think I knew myself well enough to know that I wanted to be able to build the software. Not that I would ever be the best in the world at it per se, but there was just something to like understanding how it worked to build my confidence. And so I saved my bonus for two years and then just lived off that for the next two. Didn't get a job. Taught myself to code, built a bunch of stuff that no one's ever heard of. And, you know, I think at the time again people were like, are you starting a startup? And they'd ask and the answer was like, I don't know, kind of, which is like a really uncompelling answer. If you say that people think, well, you're definitely not, like that doesn't sound like a founder's answer. But I think for me at least initially, one, it was just about developing the skills and the taste. And second, I had seen enough people working on something that they probably cared about at some point, but then sort of the shine truly wore off and they didn't really care about it, but because they'd raised money or had people working for them, they felt like they had to keep going.
And how much of a slog that is. Entrepreneurship can be a cage-making. And how, you know, we like say, oh, you know, the worst thing that could happen is, you know, everything goes wrong and it goes to zero and it's a crater in the ground, and actually that's a pretty, like, sure it's not what you want to happen, but then it's over. And actually the median outcome is it just keeps slogging along and you burn years on it.
Yeah. And so I had probably a lot, probably an unhealthy amount of skepticism on really wanting to work on an idea that I felt like would last for a long time.
Where did Dropbox come into the picture? Because I read in my notes that you were at Dropbox and obviously you must have had a ridiculous like breeding ground of, you know, incredible talent.
Yeah. So I kind of taught myself to code, built a bunch of stuff for two years. Nothing really felt right, like keep pushing.
You didn't make anything as good as Dropbox.
Definitely did not. Deeply did not. And I think I got to a point where I was like, okay, I can program. I can make stuff. But I've never really worked in a company, right? I worked at this like quirky investment firm that was wonderful, but like only sort of had co-workers. I did this stuff on my own and with a handful of friends, but like what is a company? And I had some friends who were at Dropbox. And it was kind of the, you know, height of Dropbox's power and press and it, and so got really lucky and joined Dropbox to work on what at the time was a new product there. And to spend a couple years.
Oh, I used to use Dropbox Paper all the time. I loved it. Yeah, it's quite innovative.
Yeah, there's a lot of actually kind of UI/UX things that now are even, it was delightful to use kind of thing. Pasting over a link that's now kind of more of an internet software standard. We, at least when I was there, or maybe say for me, I never figured out how to explain what Dropbox Paper was to someone besides saying something that rounded to it's more innovative Google Docs. You can use emojis in your documents. And actually, that's awesome. And you should switch your whole business or team or personal setup from Google Docs to Dropbox Paper. Like you just, when you say that, you sound a little like you've had too much Kool-Aid, but there's something real to it. And we sort of never, or I never figured out like how to truly explain it. I remember like 10 years ago Stuart Butterfield, founder CEO of Slack, had some tweet or maybe in one of his like long, you know, Medium meditation things was, the true test of a great product is how much it changes human behavior, and I always really liked that, right? And I think under that metric, like at least I was not able to get in my tenure, was not able to get Dropbox Paper to that place.
You did say earlier, you know, with reflection of the VC model and stuff, if you want to be a great operator, then also just go and do the thing. Yep. So, you've done a lot of exploration, a lot of talking. What was your moment where you were like, you know what, let's just go do the thing?
Yeah. I think it was actually when it became clear that the thing Dropbox Paper needed was to get closer to the rest of Dropbox. And I was not that product manager for lots of reasons, but like that was clearly the most important thing. And I could try to do it. I would be mediocre at best. Like I'd be B-minus at best. And there were lots of other product managers who would be way better at that than me. And I think it was kind of a phase thing, right? And if you know like the initial task was try to get this thing off the ground and get early users and get feedback and wrap that in, and you're like, okay, that I really liked and I felt like I was good at that. But the like now take that again and like connect it to the rest of Dropbox in a way that people who do like Dropbox and are logging in and see it and, you know, work with all the cross-functional teams to do that, like that was just like, oh, again, I'm going to be a B-minus. I'm going to be kind of sad as I do it, like so that's not me.
You mentioned earlier, you know, the mission-driven founders and, you know, other kind of founders, and, you know, there is no right or wrong way or whatever, but you have identified that people have to love the work. You have to do the work. You have to love the work because the work is generally a decade-long at least project. What is it about security compliance that could possibly make you wake up at night in a cold sweat as I imagine you did with a Eureka moment that went, hell god, I just can't wait to solve that problem.
Yeah. I think two things actually and truly, you know, we used to joke like in the founding story you're like, we're never going to get away with the like, ah, ever since I was four years old I've just been deeply passionate about, you know, security compliance. No one will believe that. So we don't, we generally don't try that. Except for here is that like meta point. No.
Fire engine, astronaut, security compliance. Exactly. Like isn't that what your kids do naturally?
No, I think two pieces. So one, security compliance is actually so broad, and as you, I like exploring, I can be a little bit of a shiny object person especially if I'm not careful with myself. But like this is a constrained but large area, right? And so we get to think about everything from the cloud infrastructure account at a company to the people who work there to the software they use to, you know, the laptops they use and the application anyway, there's just like whole range of stuff, and so I think it's actually a like neat horizontal and broad field versus if we were, I don't know, just building a security vulnerability scanner, which many people do and most successfully, but that it's like much deeper. So there's part of that that I like. And then I think the other part is, you know, and actually after Paper there's some of this too. Vanta as a product and a value proposition just is like deeply logical. The first time someone uses Vanta it's because they probably have been asked by a customer for a certification or a framework. They don't have it, but if they get it they will sign that customer and potentially many more. And so you're like, okay, so I will do that then. Or I can think about how much money might I get from these new customers? Should I spend the money on time to get the certification? Great. And I can make a, you know, pretty logical spreadsheet decision. And then over time, you know, you take something that's sort of like herding cats and like done in spreadsheets and takes a long time and you, you know, make it much more seamless and easy. And anyway, there's just like a deep, the way I could not explain why someone should use Paper besides saying things like, 'But there's emojis and stickers.' The reason you should use Vanta is like because you pay X and then you make 10X as a business.
Which completely get that. But how do you arrive at that insight?
About six months of conversations with folks.
So go on. You left Dropbox. Yeah. And what left Dropbox?
I think did the thing a lot of folks do who like to build, which is built a bunch of stuff that no one wanted. One of the best like...
Paper. No, I'm kidding. I'll stop messing with you.
You said it, not me. Someday. But anyway, so we built a bunch of stuff no one wanted. Then was like, oh shoot, doing this wrong. No more coding. Because we can probably, hubris, but like probably build whatever we want to build, but like that's the quote-unquote easy part. The hard part is like what does someone want? And so spent six months going deep as deep as we could with like founders, engineers, heads of security, anyone who kind of touched security. And it started just really open-ended and, you know, what do you do in your, like what would you say your job is, like what's the best part of your week, the worst part of your week, and like trying to kind of find a person with a problem. And through that got to security questionnaires and compliance and sort of saw this as the best part of their week as the worst part of their week, right? Like it's basically like the sort of TL;DR of security folks are like the best part of your week is like securing stuff, right? Either doing myself, working with engineers, like having that impact. The worst part of my week is like reporting on that, right? And so whether I'm reporting to like the team or customers or auditors, like I want to do the work, I don't want to talk about the work. But there's most, especially as you grow up, most of your day is talking about the work. And that was actually kind of where it started.
It's interesting because there is an insight there really that's so applicable for all entrepreneurs, which is where you've built such a successful money machine is solving problems people can't be bothered to do.
Yes. And that is like there's a zillion problems in the world.
Yep. And if you were to ask the questions as broadly as you did, I'm sure you used an amazing framework. But, you know, just asking really good open questions. What's the best part of your week? Right. What's the worst part of your week? Those are such broad questions. You unpack so much and there's a real art to that. When I was starting my company, Heights, I did exactly the same thing. I read a book called The Mum Test. Very well-known, you know, how to ask good questions. Yep. Basically, so you don't bias people. Yes. Right. Because you will just ask too many questions where you getting the answer that you want. Yes. And it's actually surprisingly hard. It sounds really easy to say, 'What's the best part of your week? What's the worst part of your week?' But because you've now worked at Dropbox and Union Square Ventures and other stuff, you are infected with bias and you kind of know the smart answer. So it's actually really hard to ask such basic questions and get deep insights back. Yet you obviously unpack so much that you don't know. So you don't know what you don't know. You can only get it by asking what sound like quite dumb questions, right?
Yes. And I think you do have to get a little comfortable being like, this is going to sound really dumb. But that's okay.
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Because I think one of the things about, I don't know, entrepreneurship or starting something new is it doesn't really matter what you want the truth to be. The truth is truth and you have to figure out what that is and if you don't it doesn't, you know, it doesn't work out. You slam into a wall at some point, like it just doesn't work. And so, I think for me that was so like I can sound dumb now and hopefully figure out something smart later or I can sound smart now and be dumb later. I'm like you'd much rather be smart in the long run than dumb, but actually.
So, what do you think is a better way to build a great business? Focus on what someone says is the best part of their week and making it better or what is the worst part of the week?
Worst part. Worst part. Yeah. I think there is actually, within Vanta we found this, there is deeply something to building something that does something valuable for someone that they don't want to do themselves, right? Because they will not pay infinite amounts of money, but like that intersection of I have to do this, but I don't want to is a like, can you make this go away painkiller. Right. Versus the like I really like this and like can you make it slightly better, you know? Kind of our, you team collaboration is a lot of that and why the value prop for those tools is so hard because it's like your team will work better if you use Dropbox Paper. I can't quantify that and I can't tell. You kind of have to believe that. But again, it's just a different pitch and I think it's a tougher pitch.
So you've done this interview process, you found a bunch of people saying security compliance stuff is the worst part of my week. Yep.
You were thinking, well, you know, I hate myself, so I guess I'll just do all the work that everyone else hates forever.
Yes. Yeah. Is that logic? Um, I think the logic was more like, oh, these people really don't like this, and so much so that they actually don't. Many I spoke to didn't do it. Like, it'd be really valuable if I did this, but I don't know how. It'll cost me, I don't know, $200,000 and 12 months of my time, and like I just got other stuff to do. But if there was an easy button, I'd press the easy button, right? And so then it seemed like, okay, can I, you know, like, yeah, maybe that's not what you want to do, but can I make the easy button? Can I make the easy button? Right? And then we'd go and talk to people who are doing this work today manually, and they would all say, you can make an easy button. Um, but then it's like I'm a consultant and I think about things as one-off and bespoke and there's all this nuance and so of course there's no easy button because um what I do is like deeply different based on every company. Um, and you kind of sit there and you're like, well, yeah, or like empirically that's true and I believe you believe that, but like does it have to be true? And I think there is something to like thinking about it with like more of a software scaled mindset than a like one-off services mindset. We still find that tension today.
