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

21:57You 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? It's, I think, hard to do, hard to teach. I think what I try to tell people is figure out what, like it's personal and not personal sensitive, but like personal, like specific to you. and figure out what makes you happy or centered, whatever those things are, and like do not give them up. And so for me, for years, it was like, you know, running three or four times a week.

22:40And like exercise, sure, but it was actually just like the mind-clearing catharsis kind of meditative, like running. And, you know, it was like running for me, but like whatever for someone else. And it's like whatever that thing is, do not give it up, and I don't care how busy you get, but sort of know what makes you feel like you and don't drop those things. Know what things make you feel like you, which is kind of like what you're talking about is habits and hobbies. Is that more of what you're thinking about? It's just like that feeling where you're moving through the world and you feel like you're at your best, like you're the best, shiniest version of yourself.

23:14It's like, what brings that on? So for you, running is one. Running is 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 six years old. Right. And so, like, if I think of, like, hobbies or anything I've done through my life, reading is actually one of the biggest through lines. Right. And so there's a part of that that just feels like me. Yeah, because I was looking. You read, like, I don't know, 30, 50 books a year or something. Yeah, but it's like, I mean, yes, I want to learn things and, like, blah, blah, blah.

23:42But actually it's just, like, it is centering. I feel like me. How do you do that? When I was running a company, and by the way, mine was not a$2.45 billion company, I was like, I have no time to read. Are you kidding me? There's problems everywhere. I'm drowning in problems. And did you just replace TV with reading? Is something as simple as that? Yeah. Like, actually. Eric told me that you are, like, extremely quick with reading. He's like, she would take a bus to work. Yeah. And read the book. And read the whole book on the bus ride. Yeah. I mean, over the course of a week or so. But yeah, like, actually to this day.

24:12The way he said it was more legendary. He was like, to and from, cover to cover. No. I wasn't at it. You should roll with that. I actually still take a bus to work. part of it so I can just sit there and like... You bus to work? Yeah. Because look, if I take a car, I'm just going to like sit in the back with my laptop writing emails, you know? And then a bus, like, I want a San Francisco bus. I'm not pulling on my laptop on that unless something's like really gone wrong. And so it just forces me to like sit there and have 20 minutes between home and work. And I like that much more. You know how people are like obsessed with cold plunges?

24:45Yes. I think the more hardcore version is take a San Francisco bus to work. It's like, wow, you can endure a 18-minute bus ride It was like. That's why the buses aren't bad. 5R used to be my bus. 5R is a great. Dude, I used to take the 38, and the 38 is like an actual zoo. It's like anything can happen. Yeah, yeah, yeah. No, 5R, great bus. I miss it. I miss it. Okay, so bandaging your own psychology, you said figure out what makes you feel like you, most of you, and make sure you stick with those things, keep doing those things. It'll kind of keep you centered with it. But what about, Ben, is your own psychology when it comes to self-doubt, when it comes to getting down on yourself?

25:21Because I spent two years. I didn't really land where I wanted to land with it. Did you have a conversation with yourself there or a story you told yourself in order to? Yeah, I was so annoyed. Which, in retrospect, I was, like, being so pretentious. Like, life was good. You know, again, like, the bat nut. Like, my worst case outcome was becoming a product manager at Dropbox. The height of Dropbox is power. Like, my life was great. Could you just say the bat nut? 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.

25:52Do you use negotiation terms like that just regularly? Hopefully not. That sounds kind of obnoxious. I'll try not to. No. No, I like that. I've always felt that if you build a great Silicon Valley company, internally in your company, you should be a totally normal person. But outside, you should have that like 10 % crazy. Yeah. It just gives you like actually like 2x the valuation. It just creates this extra aura. Totally true. Wow, she's barefoot all the time? Why? Interesting. She must be one of those real outlier types. Oh, my gosh. All right, I want to ask you about this list of ideas that you did.

26:21So I've looked back in my career, and even when I went through eras where I tried something and it didn't work, a lot of the times I look back with the benefit of hindsight now, and I think, oh, I was just sort of an idiot about it. Had I actually either stuck with it or done it differently or pivoted the market, that actually was a good idea. I'm curious, do you feel that way about any of the projects you worked on? Like, they're art projects, and I say that with deep love, but, like, they're not businesses. Okay. The voice assistant for biologists, yeah, that doesn't sound like a great business.

26:50That was just comically bad. No, yeah, there was, like, a deep lack of any commercials in nearly everything on that list, which I think is part of why Vanta has had commercials, like, baked in from the very beginning, because I'd made that mistake so many times. What about now? So if you weren't doing this or in general, like when you operate a business, you see a bunch of pain points, blind spots, maybe like parts of the market that are unaddressed. If somebody is listening to this right now and they are looking for, you know, inspiration or ideas that, you know, spark thoughts in their head about stuff that they could go do, where would you look?

27:29What would you recommend people think about? What problems do you think need solving? Yeah, I think so much of what I think about that's not kind of directly in band of the wheelhouse is something around like running a B2B SaaS or being in a B2B SaaS business. Forget running it, just being in it. There's like so many, like someone please fix the go-to-market tooling stack. There's 9 ,000 tools and none of it. And it's like you jerry-rigged them together in this Rube Goldberg machine and the marbles are all up on the floor. And like anyone wants a B2B SaaS? Just like fix that. Go full stack on all that.

28:00But for people who don't want me to be sass, which there are hopefully many, I think the process Vanta came out of, I mean, I, of course, I mean, I liked it going in, but now, of course, I really like it. But that was pick something you want to learn about and just go talk to anyone you can about, like, what their days are like, what their problems are like, just, like, what's going on and kind of try to develop a mental model of this space. The story I heard about Vanta, which sometimes we make up these retrospect stories. So I don't know. You tell, you can. I try to actually tell the true one.

28:32Like blink twice if it's true. Yeah. But it was, you're at Dropbox, you work on this thing called Paper, which was this, I remember like seeing Paper at the time. It was like this idea of this like collaboration tool. Dropbox's version of Google Docs. Yeah, Dropbox's Google Docs. You go to launch it and it's like, hey, we don't have Sock 2. So can't really launch or customers can't use it. And you were like, Sock what? Yep. And you didn't know really what that was. And you were like, so how do we get that? And you started asking questions to try to understand, like, what is this thing that blocked us here?

29:00If it blocked us, maybe it blocks other people. Dropbox had a security team that was going to be able to try to solve those problems. But, like, the average startup doesn't. 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 and coded them up and shipped them out there or whatever, you didn't write code for this. you were like, I'm going to test this idea with an Excel spreadsheet only. And you went to one or two startups, I think YC startups that you thought might need this. And you were like, hey, if I did this for you, would that be valuable?

29:31And they're like, oh, yeah, sure. Can you, how much of that is true? All true.

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30:43The stylized part is all the Dropbox stuff happened, there was no light bulb. I was like not smart enough to have a light bulb go over my head at the end. Wish so. But it was just like, learned about the whole process, learned what it would take, and then like 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. So the idea of like, we're going to go two years of work to then see if we have product market fit. You're like, bad. Bad. Like, how do I find reality faster? Came back to it later, did the spreadsheet thing.

31:10And I think, honestly, it's like because it's 35 things on the list. Like, kind of at the point where you're like, okay, I can write, you know, maybe it's so much shoddy JavaScript. But, like, 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? And so, like, how much of the validation can you front load there? So, I think a lot of people hear that. And, like, they hear you should talk to customers. You should validate people want this. Make something people want. I don't think anyone has any idea how to actually do it.

31:39So what is the quick and dirty recipe for how you actually go? Who do you talk to? What do you really ask them? How do you make sure you're not getting these false positives just by being like eager beaver? And they're like, yeah, that would be maybe I'd be interested. And you're like, they totally loved it. Yeah. So on the false positives, anything that is not can you do this for me now, tomorrow, next week is a no. And people are really kind and they want to be kind. And so they don't say, like, rarely do they say no. But a lot of like, oh, maybe next quarter. Like, I don't need this, but my friend might.

32:11Hard nose. Yeah, you should date my friend. Totally. Hard nose. I think on who to talk to. I mean, look, we started with, like, anyone who would talk to us. And then it was just like, and then sort of ended up being coworkers, former coworkers, because you had, like, some, like, well, I don't know if you know anything about this topic, but you're kind of a nice-ish 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, take it forward, you know, like make it easy for them and just keep going out.

32:47Yeah, I think that's an important one. Make it easy for them to do the thing they said they want to do. Oh, yeah. Like follow up and be like, thanks so much for meeting me. Like I would love to talk to your friend, Eric, who said this, like here's what I'm working on and just like assume they will, like write them an email they will forward. Exactly. Yeah. So you, have you ever read this thing called the mom test? Yes. Do you subscribe to that? Yeah, generally. 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 their problem.

33:17So all your questions need to be first about their problem. And 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. Yeah, I think that's true. Try to avoid yes, no questions. sounds just harder than it sounds. And there's a bunch of kind of user research tips, tricks of like if somebody mispronounces something, go with their pronunciation. Otherwise, they're going to like. Don't break rapport. Exactly. Exactly. Like a lot of that. Yeah, that's true. Actually, I think I do that. And it sort of is like a problem because it's kind of a know-it-all move.

33:50Right. And then it makes them feel like their mind goes over there. Exactly. Oh, am I being stupid? Did I say something stupid? Exactly. Where you just like want them to like stream of consciousness at you basically. Yeah, exactly. Do you have any good hustle stories for how Vanta kind of got the flywheel going? Because, you know, startups don't kind of just like explode right away necessarily. Yeah. And I've seen your like ARR chart, which looks like a beautiful hockey stick. Yeah, totally. But if you zoom in, it's like, wow, that was a year where it's like pretty kind of small. And then it started to accelerate.

34:20Was there anything you did that you felt was interesting, unique, that kind of took hustle or creativity? Tiffany. It's so funny looking back because, like, I sent a bunch of outbound emails to YC companies, but I didn't know the word outbound at the time, right? I was, like, emailing YC founders for feedback. And I legitimately did want their feedback kind of to this. But it was, like, half a, like, okay, I'm going to spend, you know, 60, 70 % of the call talking about the problem and how you're solving it. And then in the end, be like, I am building a thing. Would you like to hear about it? But it was, like, totally called outbound.

34:52You know, I just, like, didn't know that word. So you emailed a bunch of YC people. That got the ball rolling. What happened after that? Honestly, the early strategy was like just do and try everything and then see what works. So what did work? The outbound worked. There was a word of mouth. We tried actually really hard in the early days to basically build this call response and like founder Slack channels or VC Slack channels where someone said Sock 2 and someone else would say Vanta. And you just wanted this, you know, Sock 2 and Vanta. You're saying like build the brand in people's minds. Yeah.

35:24And that was great for a while. and then a bunch of knockoffs came. And anyway, there's a bunch of other ways to get socked too. And so that association... I remember you guys had a billboard. It was like, what is it, compliance that doesn't sock too much? Yeah, still up. That was good. Still up. Yeah, I joke with people. Like, we make software, but like we also make a billboard and we're equally known for both. We're like equally as important. What else? podcast advertising really worked I mean actually it still really works but like really worked in the early days I thought podcast advertising was just gonna be like sending money out the window I was totally wrong and that's what happened somebody on your team pitches you this Eric Eric was like I want 20k to go on this week in startups or something and I like rolled my eyes and said fine whatever go it totally worked he was totally right Eric is like this mythical figure to me now where I've only ever heard great Eric stories.

36:25And so I don't want to hear any, if anybody has a bad Eric story or an idea you had that didn't turn out true, don't tell me, please. No. All right. I want to ask you about a couple other 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. Oh yeah. And people read a lot into this. I'm just like joking with myself because I say contact me through these four ways that are all have totally different names on them. Oh, okay. So like it's just like minor.

36:54Naming consistency is overrated. Yeah, it's just like minor self-awareness thing that I think people think is meant to be a broad philosophical statement. Do I actually think it's a broad philosophical statement? No, probably not. I think Vant has taught me consistency is actually underrated. Yeah, I was going to say, you strike me as somebody who's consistency first. Yeah. It's bad when the goalposts move. I don't know if you're saying you think this or that other people think this. I think other people, the advice tends to be right, Like, you know, if your goalposts keep moving, it's hard to find happiness.

37:23And, like, you're always finding happiness. Explain what it means. So, like, what does that even mean? The goalposts moving. Yeah, like, I mean, it's a lot in lots of forms of life. But, like, let's take startup founders just because, right? It's like you want to start a company. You want to hire some people. You want to write the seed round. You want to get to, like, a million in ARR. But then by the time you get there, you're like, actually, I want to get to 10. Right, that's it? Yeah. Yeah, and there's, like, always something you are chasing. and I think that it's generally seen as a recipe for unhappiness, right?

37:50Like, why can't you be happy in the moment? You did this thing prior you thought was great. Like, why can't you think it's great? And I think that can be true in some cases, but I actually think or I think that the trick is slash downside is if you're, like, only happy when you hit a goalpost and then you're moving them, like, you'll never be happy. if you actually just like the work. Right. That's what it doesn't matter. And I think a lot of things are more sustainable when you like the work, especially when you have a lot of work to do. My formula is progress equals happiness, which is that no matter where you are, it's sort of like the Y intercept doesn't matter, the slope matters.

38:30And so wherever you're at, if you don't feel a sense of progress in your life, you will feel unhappy and then you'll feel even worse. You'll feel guilty for feeling unhappy. Yeah. Because you're like, I guess I do have all these good things in my life, but I still don't feel this way. I'm just fundamentally broken inside. I'll never be happy. When in actuality, it's just a sense of progress. Even better, a sense of progress in a direction that you have set out intentionally that you care about. Yep. And I think that in that sense, moving the goalpost is great because you're saying, I would like to continue making progress.

38:57I enjoy progress so much. Why would I stop my progress? That stops my happiness. Yeah. It's a different way of looking at it. Do you remember, deep cut, 10, 12 years ago, Jess, who was founder of Polyvore at the time now at Sequoia, wrote a blog post about founder psychology? No. What did it say? It was like basically like why our founder is always unhappy. And she's like, especially when their companies go like this, and it was a line up into the right. And she's like, because if you zoom, you know, again, Y axis getting higher, like what is this? Because if you zoom in on the graph, it doesn't look like a, you know, 45 degree angle.

39:31It looks like a roller coaster that is going slightly higher. Right. Right. But it's like the roller coaster along the way. And, like, you know, again, even when you zoom out and you've got this lovely 45-degree line, the downs hurt every time. Yeah, it's the peak to trough that you feel. You don't really even recognize that you've gotten higher progressively each time. You also have another one, which is high standards are bad. You think that in generally – you said people don't say this, but they imply it in different ways that, you know, don't have such high standards. Right. What's the situation where that's come up for you or you've felt that?

40:04I think a lot of Vanta stuff and I think within the company and then with, you know, kind of partners or folks outside. And I mean, some of the feedback we get that like I kind of appreciate more than anything else is like people care. People respond super quickly. Like, you know, again, something might have gone wrong, but the person tries really hard to fix it. Right. And I think those things definitely don't happen everywhere by accident. And 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.

40:42Like, kind of scary. Did I join the right place? Like, what's going on? What's an example of that? Where would somebody feel that? A couple places. But I guess in go-to-market, our expectations around quota, around attainment, they're way off industry. They're way higher. And I think if you just, if one just hears them in a vacuum, they're sort of like, what is what? Like, why would I sign up for that? Then they join and it's like, oh, because you're surrounded by people who are like into what they do, getting better every day, want to get better every day, care a lot. And that sort of environment can be like really infectious.

41:16I'm curious. Did you ever read this leaked production document from Mr. Beast? You ever take a look at that? Did you see that going around like a few weeks ago? No. You know who Mr. Beast is? Yeah, yeah. Yeah. So like right around the same time that Paul Graham put founder mode out there and founder mode, like, but wait, what is it exactly? And like, I think, yes, but what? Part of a lawsuit, Mr. Beast, like the internal doc he wrote for his production team leaked a big part. Like we've gotten to know him and become pretty friendly with Jimmy over time. And it's just like the number one thing, you go hang out with Jimmy for a couple of days, like you walk away and you're like, oh, he that's what people that's what it means when people say, you know, Steve Jobs used to have this reality distortion field.

41:56Yeah. And it's and literally he his company is based in like a tiny town in North Carolina. So like he gets people to move there. And then once you're there, you're in his bubble and in his bubble, the expectations of what work is, about what success is, about what we're able to do, about the timelines we do them on, about what it means when something says no, not possible. And he's like, one of his things, he's like, push past the no. He's like, you know, you have to be able to push past the no. You don't always have to get it to be a yes. But like, if you just come back and you said, oh, we, you know, we asked for the permit and they said it's going to take six months.

42:29And he, like, that can't be the end of the story. And we saw it on every little thing. Like, for example, we wanted to play basketball the next day and it was midnight. And somebody was like, oh man, I can't wait till tomorrow. Like I just want to play. And he goes, well, why do we have to wait? Like, well, it's midnight, Jimmy, what are you going to do? He's like, I'm sure there's a gym around here somewhere. Let's go, let's go find one. And we're like, yeah, but they're going to be locked. It's midnight. Like schools aren't going to be open. He's like, call the athletic director. He's like, just call, call all of them right now in the county.

42:55It'll take us 20 minutes and offer any of them a thousand bucks. See if they'll come open it. And like part of it was like, oh, he just throws money at every problem. But actually it's not about throwing money at it. It's yeah. Everybody else would immediately just default to like, this is not possible, not feasible, not not going to be doable. Whereas his default assumption on any given thing is like, why not? Of course we could do that. Yeah. It's just a matter of deciding if we wanted it, we'll do it. If we don't, we won't. But that's it. And you just see that time after time after time hanging out with them on big things like, you know, the videos that they're going to shoot, but the small things.

43:25And it's just a different gear. It's like, oh, your gear is like my stick shift only goes to six. Yours goes to nine. Right. If I'm going to hang out with you, I now need to decide like how I'm going to get to eight or nine because otherwise I'll just be sticking out. This won't be the right place for me. Yeah, totally. And I think there's a, I mean, I think also if you like experience that and you're like, you know what, I'm go with six. Right. Totally reasonable decision. Like not that, you know, arguably maybe a better decision in some cases. It's like totally fine. But the like, there might be, there might be a nine for any given thing.

43:58I think it's a helpful mindset. You also raised a bunch of money late, so you didn't raise early on. You got to$10 million in ARR before you went and raised your Series A. I'm not so curious as to why you did that because I'm guessing the answer is pretty simple, which is like 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? Oh, it was really fun. Yeah, it was great. It was really funny. So people, or VCs in San Francisco, broadly, like knew we were doing well because of kind of the Slack channel chatter, like Advantage had come up.

44:36But they sort of didn't know how well. And so there was one pitch meeting. I remember they. And sorry, you kept it low-key, right? On purpose. Yeah, kept it low-key on purpose. Because basically we were like, we have this great idea and everyone else thinks they can't even like spell what we're working on. Think it, you know, has K's and do things on your feet. and I would rather they not know because then somebody's going to start knocking this off and copying. But anyway, very smart VC, very good at his job. Like, go and pitch, and I start walking through the slides, and I get to the ARR ramp chart, the, you know, 10 at the end of it, basically, and his jaw just dropped, and he was, like, clearly speechless, and he's looking at it, and he's like, I thought you were at, like, 2 1⁄2.

45:18And you're like, no, that was, you know, 10. And he's like, keep going. And at the end, he was sort of like, we're not going to, like, we missed it. Like, we're not going to be able to do this. I can, like, try to introduce you to someone else. But, like, you know, it was fine. Like, you know, there were other people. But it was this kind of interesting pitch experience. And then, basically, I go into a meeting with another VC who's very good at his job. And he's like, you know what? I thought you were at 9.4. Because I'd, like, taken your Twitter chart and backed it out and taken the points. Yeah, I did the same, actually.

45:46And, like, counted the pixels. And I was like, well, you weren't putting your job. I did the proportions. She said 10. So if this is 10, where was she a year ago? Get 2.7 or whatever. He had basically done that. And that was also, you're like, oh, this is great. It's so good at your job. So fun. Is that who you end up going with or no? No. You're great, but Sequoia's gone. But I think actually it was, until the goalpost stuff, and I'm not very good at celebrating, but it was a moment where I took a week and I was like, no, I'm going to tell this story and what we've done and, like, I'm deeply proud of it.

46:25And I would have told you that, but now I, like, feel overwhelmingly proud of it, right? And, like, here's how the pizzas fit together. Here's how they will fit together, and I believe it. And so that was just, then it became, like, I still kind of hate fundraising, but it was talking about something I believed in. Just fun, right? Eric told me that he thinks you're great at negotiating. It's so funny. You said that's surprising to you. But he was not wishy-washy about it. 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.

47:00Yeah, no, it's really surprising. I think if I'm confident, I'm actually confident in it. And then we'll just stand and like not blink, not swerve if we're playing chicken, won't eat the marshmallow. It's like, I got it. Like, let me know when you want these terms. I'm happy to sit here and wait. And actually, truly, I'm like happy to sit there and wait at that point. So I think it's just a lot of that. It's like I won't – if I believe it, I won't flinch. Cool. Well, thank you for doing this. This has been amazing. Where should people find you, find Vanta? Maybe give it a shout. Yeah. Vanta.com, V-A-N-T-A.com.

47:34If you need any help with anything security or compliance related, we would love to help you out. Awesome. Thank you for doing this. Thank you so much.

47:49Let's travel, never looking back.

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