Carolyn, I am so excited. Today we have Christina Cacioppo of Vanta, the founder and CEO, the trust management platform. Welcome, Christina.
Thank you so much for having me. I am so excited to catch up with you today because first of all I was recently listening to a podcast and you were talking about what Vanta does, and just for laymen, because sometimes you know my family in Boston listens to this and they're not technical, when we describe it as a trust management platform, I'm going to dumb it down a little: cyber security and compliance automation. Dumb down even more: securing customer data.
Yep. Helping companies build out their security programs and then go get credit with their customers for all that work. So maybe through an audit or a questionnaire or like a status page, but like you did all the work, get credit for it with your customers.
I was listening to a podcast thinking, "Oh gosh, I got to sort of learn about this." I was gripped in the same way I was gripped with Flexport. Caroline, do you remember how into learning about like container shipping I was?
Logistics. I became so fascinated by this industry, this category that you guys created. So, we're going to come to that, but I want to go way back cuz actually our paths crossed a long time ago. Did you used to come to demo day when you worked at Union Square Ventures?
I did. I would come, I got the one of the perks is I got to go to demo day and I remember meeting you there. Yeah.
What year was that? Like bring us back to back then.
And you had already graduated, like you were how old?
I was summer '10. I was 24.
I had done, unlike most of Silicon Valley, I did extra school. So I did like five years of a bachelor's master. So I was like basically one year out of school.
And you were from the Midwest.
So it must have been just mind-blowing to arrive in Silicon Valley back then.
Stuff was happening. It's funny. I was totally the girl from the Midwest where I remember even admit weekend and just being like the sky is so blue, you know, and like 60% of Stanford students are from California, right? So just like what are you talking about? But it was I don't know. The sky is more blue in Northern California than it is in Ohio. Like kind of ever.
Are we just optimists when we live there? Also that probably.
Well, also there's no hills in the Midwest, right?
Right. So, it's like it's also super flat in, it's not very, it's not flat in Northern California.
Yeah. No palm trees.
How did you land a job at Union Square Ventures?
Dumb luck. Truly. You know, one of the many things I respect about the USV guys is they've always hired off the internet. And so I'd started reading Fred's blog and at some point in the summer of '10, in like spring, like March or so, he'd written this post and said, "Hey, we've had this analyst for four years and he's great, but he's moving to Boston, so we need another one. If you're interested, send us some links to your web presence." And I read that and was like, "What even is this?" This is 2010, right? You're like, "What?" like this both sounds great and like who is going to get this job? Like what crazy person? And sort of had that mindset about it, but kept thinking about it. Then of course, literally 30 minutes before the like form was supposed to close, I sent four links to my web presence. No other words, nothing else. And they hired me.
What was your web presence back then?
Fair question.
It's funny. It was 2010. Flickr, Twitter. I had just, my like year after school I'd spent in Berlin working at a design lab and I'd like kept, I started a blog because I wanted to be like a design blogger and so I had this like Streets of Berlin, not very good to be clear, blog. And it was maybe a Tumblr but it was basically that.
Okay. I wonder if you had more web presence than the average applicant, you know, like cuz I'm just thinking like that's a lot of kind of cool stuff.
I think there was some of that. I think also, you know, in retrospect, I like knew people at Stanford who knew them. It was not like, didn't, that didn't even occur to me to use any of that, which was kind of, kind of silly and very naive in retrospect, I think. But just kind of makes me like respect those guys even more cuz like they truly did hire off the internet and like yes it ended up being a Stanford person but it wasn't, you know, was not a Stanford connection.
So I want, I want to ask you first of all what you remember from the early demo days that you came from. I'm just curious. And also I want to talk about your time at Union Square Ventures because I feel like you learned some, some good lessons there.
Yeah. Okay. So early demo days. So, these were in Mountain View, like that building,
Pioneer Way. That was our office, I think.
Yeah.
Yeah. And I think actually I have, I still have my like list of, I kind of want to pull it up, but like there were probably 40 companies max in the batch. Is that right? 20, 40.
And I think we'd go in and I remember going in when it was sunny and we'd leave when it was dark. So, whatever that, you know, I don't know, started at 5, 6 p.m. I think when I started the pitches were like 3 and a half minutes or so, maybe four.
So, I'd sit there with my like notebook and your print out, my pen, and I'd like write notes on each company and I'd sit there, you know, and like try to figure out which were in USV's wheelhouse, large networks of engaged users, right? And then, and so you'd like do this and I also remember Paul in the beginning doing, getting up and being like, okay, like you know, you're at YC demo day, like there is an Airbnb in this batch. I don't know what the Airbnb is. This is your job to figure out, you are smart investors, but like you will find the Airbnb in this batch. Like now we will start.
Yeah it is. It was like kind of like a circus ring leader but in this incredible way. Like it was this like, and now the show will start. It's all demos and I'm like scribbling notes and then there was like a cocktail hour. You didn't call it that, but there was like a cocktail hour,
Like beer and buckets and some wine.
And I remember my thing was like, okay, you know, like we're not going to drink, cuz like I'm at work, but you're going to go around and I was, I always kind of tried to be basically the last one in the room, like the last investor. And so I remember like, I don't know if I quite made it, but I think I was like in the, you know, single-digit count of investors left, right, and just trying to like talk to folks who were like, not about like, not interested me, but like really interested in USV. And you're like, yeah, yeah, I understand, like let's talk about USV, we do that. And then it would be really dark and around 10:30, 11 p.m. And I'd like get in my little rental car because again 2010 and like rental car myself back to the Hilton or whatever it was and then wake up the next morning and like type up all my notes to this email of like here's all the companies and like, and then here's like the three or five that I think were interesting. And then inevitably I'd get an email back and be like no those aren't, like this other one is, you know, and you're like okay cool I'll like try to go set that up. But it was very fun.
Do you remember any big win? Yeah. Did you pick a winner? Did you find the Airbnb? Because we all know Fred Wilson passed on Airbnb.
Yes. That he, he famously acknowledged.
Well, I was going to say when I walked into USV in 2010, the cereal box wasn't on the shelf. Like that post and that story. It was not, it's true that cereal box sat on the shelf. So that's very true. No, I definitely didn't. There were a couple companies I really liked and I didn't get them to invest in and actually got to know the founders and now they're friends but like they were not, they were not in the top whatever exits of YC. So, you know, USV was more right than I was, deeply.
You must have like learned so much working at that firm and meeting with so many founders. Like what, what do you remember as like high points from your time as a VC?
Yeah. Actually, before I answer that, can I give you one more YC demo day?
So, okay. So, I'd go, you know, winter and summer and, and show up and kind of rerun that playbook. And I think it was summer '12. I was, I think it was a two-day demo day or like a two, a split.
Yeah. It was a big batch.
Yeah. And the day I was there was the day Steve Jobs resigned from Apple for health.
And that happened like in the middle of someone's pitch.
Oh. And I still remember sitting there and there's enough people with iPhones and people just are whispering and like the poor founders who you know were like, and then basically like they finish and I think somebody's like we need, we need a moment, you know, like Steve Jobs just left Apple. And I remember getting that news sitting in like the demo day folding chairs.
You were in the Computer History Museum at that point. I don't remember that at all and I'm...
I don't remember either, Carolyn. I'm pretty sure I'm so glad you told that story cuz what a moment.
And it was kind of, yeah. I think we knew enough to be like, "Oh, this isn't good."
Like this is not, this is serious and not good. And who knows what happens next. He's not coming back.
Yeah. But like this is not, this is not a man who would do, you know, who wants a vacation. Yeah. Who would do this if he had a choice not to.
What an interesting memory.
So tell us about your, some of your important takeaways from Union Square Ventures.
Yeah. So, I think kind of building off some of this, I think one of the primary ones that's sort of underrated is there are so many ways to be a founder and so many ways to found a company. And which sounds like vanilla and milquetoast when you say it, but like I think I like deeply didn't, you know, like in my head it's like oh no you've got to like start programming in year four, go to college, study CS for like a semester or two, drop out, maybe wander in the wilderness, maybe just like make something then a billion people use, but like right, and then you just go do that. And like people do that and that is wonderful. And then like some people do that and some people are college professors and some people are lawyers and like everyone finds their path, you know, and like that, like a slightly more sophisticated model, but that was like basically my model of the world. And I think, you know, among the many things, one of the things I'm really appreciative of USV for is I worked there for 2 years and I probably met five founders a week on average for, you know, 104 weeks straight. And so, you just meet so many people and see so many ways of doing it. And that was really helpful I think for me because it kind of broke that like oh I don't have that, you know, I don't have that history and so here go, I should like, should I be a lawyer? Not quite, but like should I be a university professor? And I was like no, there again, there's, there's lots of ways to do it. You should do it for a way that works for you.
I think that's a great observation because I feel like I noticed that at Y Combinator, you like, there's so many different paths to becoming a founder and different types of people and different ways they behave. So it's good to, good to reinforce that. Because it means you could someday be one, right?
Quick question. Oh gosh. What was it? Hold on. It was at the tip of my tongue. It was a random question about being a VC.
What do you do as a young person as a VC? Cuz like no one wants to talk to you like that.
Right. Because you're not the check writer.
Exactly. Yeah. And they shouldn't, right?
Was that hard? Did you have to do a lot of sort of cold calls to startup founders?
No. So USV wasn't that. They, I mean I joke but like in, again in two years they probably gave me like four weeks of work, like actual work to do spread over two years. So there's a lot of like figure it out. And I think in the beginning to that, and like you know PG has essays of like don't talk to the young kid at the VC firm which I think is generally correct. I think when I was in that role I was like oh that is right. Why would someone talk to me? What is it I'm supposed to be doing here? What would I say my job is? And I think it took me six plus months probably but what I figured out was like yes no one wants to talk to me. They want to talk to Fred, to Brad, to Albert. Some people unfortunately get stuck with me. Sad for them. But like my job is then not to pretend I'm Fred because that will annoy everyone. I am not. Right. My job is to be like let me try to understand you founder, your company. Translate that into USV language. Route you. Everyone wants to be with Fred because it's Fred and he's wonderful. But like if it's a dev tools company, they should actually talk to Albert. Do that. Then go to Albert and be like, "Albert, I met Jessica. She's working on blah blah blah. When you hear it, you're going to think A, it's actually B. Like, and then this is going to happen, but like this is, this is why I think it's interesting. Can I set you up?" And kind of do the same to the founder and be like, founder, you're going to explain this. They might get caught here, so just know that and like da da da da. And then like make that meeting work.
Yeah. And like that I think that was when I felt like I kind of, I don't know, hit a stride. It's a big word. It was a big phrase, but like it's like, oh, okay, I think this is useful. Or given this role exists, I think this is a like reasonable way to play it.
And I think that would be really interesting if I were 22 or whatever.
You know, in my early 20s. Now, I want to ask you about probably what I'm most fascinated with about you because it's something that we advise all the time and no one actually does it, which is you taught yourself to code. And I know you've talked about this before, but I really need to hear it again. Tell us about how you decided to do this, what you did, that kind of thing.
Yeah. So I think in that like meeting lots of founders there's lots of ways to, to do this, I can do this too. I had one, well I probably had several but I had like at least one really big hangup and it was that I couldn't code and I wanted to start a software company and couldn't make software. And logically knew, I mean again having met with lots of people, like lots of people who can't make software start software companies and can be exceedingly successful. And I just felt like that's not me for good and bad, like, but like a deep truth about me I think was like I don't feel like I am able to do this unless I can make software or able to try to do this unless I can make software. And also as I was leaving USV, Fred said something to me which is like, Fred is, he doesn't always come off this way I think, but he is exceedingly perceptive. And I remember talking to him and him being like, oh you're not a fake it till you make it person so like don't try to do that, Christie. And sort of being like, "Oh, is that bad?" You know, like deer in headlights. But I think it's also like just very true and something that's worth, given that, worth embracing. Anyway, and so what I did was I had saved my bonus, which USV at the time had, had bonuses, which like you know tech jobs generally didn't. It was not like totally a finance bonus, but it was somewhere between, you know, finance bonus, like classic finance bonus and no startup.
Which by the way is another bit of advice I always give to young people, like if you want to start a startup, what's my first bit of advice? Learn to code and save your money.
Yep. And so what I did was I quit USV and I lived off my bonus for a year and a half. And everyone else thought I was crazy. It's like I, and I think maybe it was a little quarter life crisisish, but you know, with, with some life, right? Exactly. You know, as, as those seem very important when you're, you know, 25, right? Right. And was like, "No, I want to do that." And people like, "Are you starting a startup?" And I'd be like, "No, I'm coding." And they'd be like, "So, you're going to go to a master's program?" And I'd be like, "No." And they're like, "You should really, you seem confused. You should get an MBA." Right? And then I was kind of like, but then I have to pay $200,000 on top of living expenses to like do what I'm doing and also like have more random flights to VISA or something, you know, like not, not my jam. Right. And but I couldn't also like, I also seemed confused because I couldn't actually articulate what I was doing besides like I want to learn to build software. And people are like for what end? And you're like unclear, like hold my beer, I'll get back to you with like sort of my answer.
So you, how were you teaching? Were you taking like online courses or what, what is that, what you do?
So this was the year, this was like the era of like all the coding boot camps, but I was sort of like, do I really, like I want to try to do this myself. So where I started was Steve Huffman's Udacity course.
What I love all of this YC overlap with especially with Huffman. Oh my god. His Udacity...
His Udacity course which was how to make a blog in Python. So, I watch it and you basically just like type what he tells you. He makes this blog in Python. And then I was like, "Okay, well, you know, I don't really have a startup idea." But I was, and I'm still really into books and reading and bookshelves and if I like go into someone's apartment, I just kind of want to look at their bookshelf. You like learn so much about them from their bookshelf and then there's like lots of jumping off conversation points, whatever. So, I was like, "Okay, I'm going to make a bookshelf website." It's also why people thought I was having a quarter crisis cuz like, you know, not, they should be like, "Are you competing with Amazon?" I was like, "No, no, no. I'm making a bookshelf website." Again, and they'd be like, "What are you doing with your life?" But anyway, so I like took my blog where you'd like post to a blog and you're like, "Oh, you post a book to the blog." Okay, you post a book to a shelf. And then I made this web app that was, you know, lovely in some ways and like deeply terrible in the ways your first projects are always deeply horrible. 5,000 line main.py file, like, you know, you, you kind of mess everything up, but you learn along the way. And so that was like the very first thing and I built it and it worked.
And I had like lovely and wonderful friends that would like go and like shelf five books when I asked them and you know they'd hit some error and I'd be like oh I don't, you know, whatever, I have to go fix, you know, right? Like it was that, but like then I got to see their books. And it was like the first like, oh my god, I made that while, you know, and it took I don't know 3, 4 months cuz I didn't know what I was doing and you didn't, I didn't know how to de-, like not only like I just didn't even know how to debug, like the meta of debugging all of that, but like I don't know, you slug through it mostly.
Yeah. I just like, it's just so amazing because so few people actually do that. They think, "Yeah, I'd love to learn how to program." But they won't slug through it. Including myself. I have said for so many years I should learn to program and have I done it? No. Because it's hard and time-consuming. But you did it and I think I heard you describe it as you treated it, the process as a job, right?
Kind of to the like should I go to school for this? It was like no, but I need to, you know, like not get up and be like I'm tired today. I'm going to get up two hours late and maybe I'll put on shoes. You know, you're like can't, can't get to that. Like am I perpetually on vacation land? And so New York Tech was small. Chris Dixon had just sold his company Hunch to eBay and they had moved to new eBay New York which was this like nine quadrillion, not a real number, but like nine quadrillion square foot space that was empty. And he was kind of in the mold of like right before he went to Andre and a little yolo I think. And so it was like whoever wanted to come hang out in the Hunch office he would just give you a desk cuz he had acres of desks. And so, and that office was basically across the street from USV. So, my thing was like, look, I'm just gonna get up and I get dressed and I like walk to the same place I've walked for two, you know, like I just like basically do the same thing I've done for 2 years. I just sit across the street and type, but I do that from, you know, 9 to 6, 9 to 7, right? Like it is a job and I show up every day in a place where people show up every day and type things.
Did you ever think about leaving New York just to save money? Because that's, I'm sure your whole social circle was there, but like you know it's expensive place to live.
Yes. I think I was too, like losing the social circle was hard cuz you're like I just blew up everything else in my life like should I, should I totally do it or like hang on to the shreds I have? But it is funny cuz it was, you know, I call it like it was grad school and that, you know, like don't really go out to eat, did not get in a taxi for a while, you know, like all of that.
I have to read something. I try not to do this, but I found something that you wrote, you blogged about this on your website as you were in the middle of this. And Caroline, I have to read it to you because I swear, Christina, this could apply to someone today. And I feel like it might inspire some people. I'm going to read a couple of bullet points. If you've left your job to make things, figure out a way to explain that to your parents. When you don't have a job, most people will assume you're not working. Don't be mean to those people. They're confused, not malicious. Like most decisions, this one wasn't as risky as it seemed. If you're the sort of person who can afford to quit his or her job to make things, everything will be okay regardless of how this all turns out. And then lastly, I'll just read this one. That said, this is one of those things that's easier to do in college than after, and it's easier to do without a family than with one. But whatever your situation, thousands of other people have done this. Given time and effort, you can, too. I just love that.
Oh, I want more people. Straightforward.
Yes. It's such good advice. I mean, feel like anyone thinking of doing a startup, learning how to code, should just paste that to their mirror in the morning.
It's funny to hear that because I can both hear the I am definitely giving myself advice and a pep talk in writing that and the like kind of eye of being like stop thinking I'm not working cuz I don't have a job. I am working hard, you know, and like I can, I can kind of hear all of that.
And, and you read it. Maybe we'll train other people not to assume you're not working just because you're learning how to code because I think that that's the most, I'm like envious that you did that. Basically, this whole questioning is like I wish I had done that in my 20s when I had the time. Okay, so now you, you're learning to code. Tell us what happens next in your startup journey.
I make a bunch of stuff that no one uses. Lots of stuff. I have a list of it on my website now on purpose. Because I think another thing, backtracking a little bit, but another thing I learned at USV is sometimes on purpose and sometimes not, a lot of these startup stories are told as these linear I did this and I did this and then I had a billion users and like then I was a success. And at USV, I got to see some of those companies. And while they did this and that and they have a billion users, the in between is like not a line. Like the in between is like a crazy topiary maze. And in the vein of like kind of lots, there's lots of ways to do it and humans do this, not just like, I don't know, gods, like I feel pretty strongly about talking through the messy middle of things. Anyway, so my messy middle is, yeah, made a bunch of stuff no one wanted, was quite sad about that. Because as much as I told people, oh, I'm just learning to code and I don't want to start a startup, I definitely wanted to start a startup. I think I just didn't want to start a startup that I didn't believe in because I saw people do that all the time and I saw how it is awesome at first because you're in YC and then you raise money and then you have to work on the thing, you know, like then it is, then it is terrible. So I had probably somewhere between a healthy and an unhealthy skepticism of that. I got to a point where I, it was probably two years. I did not have a ton of money in my bank account and was kind of like, man, I am tired of bodega sandwiches, you know, and like bike rides, you know, like I feel like I'm very old now in retrospect. I was probably not that old, but I felt, I felt very old. I felt like I'd gotten to a place where like, oh, I can build something. Like, you know, is it the best thing in the world? No. Or you know, but like I can get the thing in my head under a screen for feedback that then I can make it better. So, you know, kind of box check there. You can always make it better, but like we're at some baseline level there. But like what am I actually doing? My friends, my peers, whether they were founders or working at companies, they were like advancing, right? And here I was and I'd kind of never worked at a company. Again, I'd worked at USV, but it's a five person venture firm, and you all know how USV works, and it's like wonderful and lovely and like not a company, right? And I only sort of had co-workers. And so, there was just this also part where it's like, oh my gosh, how unsocialized am I? Like, how do I, like what is a company? Like, what? It feels like everyone is so far ahead of me and I think I can catch up, but like I'm also not even in the stadium. Like, I'm five zip codes away right now.
And so there's like a bunch of feelings and emotions and sadness around that, but I think it was also like, well, what am I going to do about it? Like, you know, like, am I going to keep staying five zip codes away? Am I going to like try to get in the stadium? And so I ended up joining Dropbox as a PM because I basically had a bunch of friends who worked there, including a startup I had tried to get USV to invest in and they didn't, called Hackpad.
Oh yes, I remember that. Yes.
Yeah. And so I joined the Hackpad team to work with the Hackpads.
What were their names again?
Igor and Alex. The Hackpad founders. I definitely remember them. Okay, so you worked on their team at Dropbox. Another, you know, YC connection point here.
Also, I need to throw in here. I met you on a more personal level around this time. I'm gonna ask you when because I don't remember because you were dating Patrick Collison of St...
Yeah, it's actually reverse. You introduced us.
What are you talking about? I'm about to fall out of my chair almost. Okay. Tell me the story of how we introduced you. I'm all ears.
So, summer 2010 demo day. Oh, I think you come, you come find me and say hello and it was like oh USV told me they hired you like hello like anyway I was like oh this woman is so nice what's, you know, and then like somebody pulls you away and you're like here's Harge, Harge is also great, and introduced me to Harge because he was a partner that he was a good partner then first and we talk like go ways whatever and then like three weeks later I get this email being like hi Christina, like, my name's Patrick. I want to pitch Fred, but he's out of town, and so I figured I'd email you. And also, Harge and Jessica told me you were nice, so like want to get coffee.
I was hitting you up for business, not, not for personal at that point. At that point, cuz I would have remembered if I had officially set you up.
No, but it was the, yeah. Everything goes back to the summer 2010 time.
It really does. Oh my gosh. Oh my gosh.
So, he emailed you cuz he wanted an in to USV and I'm glad I had met you and I said, "Oh, email Christina."
And then, you know, you started dating. You guys hit it off a year, year, two years later.
Okay. Couple years later.
Oh, so there was, okay. There was a lag.
So, did he inspire you cuz he had at that point started Stripe? Like did he inspire you to, you know, learn to code and that you could do it and maybe start your own startup kind of thing by what he was doing.
Yes. And I think just one of his superpowers in life is believing in people more than they believe in themselves in the moment. And I think I was a beneficiary of that. But I think if we like listed out the people who are beneficiaries of that, like the list is literally in the hundreds. Yeah.
And we all need friends like that. It's so great when you meet someone who's like that. Oh, Patrick.
Well, can I, can I ask like going back for a minute? You, so, you're totally self-taught, right? When it comes, okay. You must have gotten really good though because like if you're, you're a recruiter, you're hiring person at Dropbox and you have all these resumes and you have MIT grads and Stanford CS and it's like how do you as a self-taught coder get a job like that?
Like I didn't. So two things. One, as a product manager.
Okay. Yeah.
The, to your point, the recruiters did not know what to do with me cuz I did not look like things they had seen. And so it was funny. So I went through two or three days of interviews cuz I was kind of doing two or three roles worth of interviews.
And then you're like why, why did they even care this much? Like...
With much respect, the recruiters didn't. But I just kind of knew enough people in good standing internally who were just like, "No, figure out what to do with her."
And I was kind of like, "Please figure out what to do with me. And if you need me to run through five obstacle courses, I am here for that."
And so then like went through all of these, there was like a, there was a bit of an engineer. There was like this prototyper role. They had, there was a PM, there might have been designer, you know, like it was just like go through it all and then see what's left at the end. But really it was, I mean I did well enough I suppose but really it was the people on the inside pushing for me honestly.
They knew you were talented and they were like, they let her just hire her, she'll figure it out kind of thing.
Okay. Okay. Yeah. But still you must have done a good job teaching yourself to code because like...
She did. She being humble.
Okay. I was going to say...
Okay, now we're getting...
