Founder Mode: Christina Cacioppo, Founder & CEO, Vanta

0:00Carolyn, we are here today with Christina Cassiopo at the Y Combinator Founder Mode Retreat. Hi, Christina. Hi, Christina. I love doing these in person. It's fun talking face-to-face. Now, Christina, we have in the hopper, we have already taped your long-form regular social radars interview that's going to be launching pretty soon, which was awesome. Yes. Don't you think, Carolyn? It was. But so today we're just really going to focus on talking about founder mode stuff and get your thoughts on it. But first, will you tell our listeners about Vanta? Yeah. We help companies build out and demonstrate trust to their customers.

0:44So practically, that looks like compliance certification, security questionnaires, trust centers, security programs. I remember being super obsessed with all of this stuff. I was like, I never thought I'd be so interested in it. But it's the kind of thing that was very unsexy, right? that companies didn't really want to spend the time or money or energy, but they had to. So tell us a little bit how you got started on this. Yeah, I've heard someone call these schlep businesses. Schlep. That's a good business to be in. Yes. Which actually I do think it's like Vanta sits at this intersection of your customers or your industry will make you go through various compliance certifications.

1:25And so it's necessary to like build the business. But it tends not to be what gets a lot of founders or folks out of bed in the morning. Socks too, right? Exactly. Okay. And so you're kind of at this intersection of people have to do it, but they don't want to. And I think one of the really striking things is people were really appreciative about our early product, which was terrible. But they liked it so much more than they should have. Because again, it just did this thing they didn't want to do themselves. You have to tell the story about Segment and the spreadsheets and stuff. Yeah. So in the early days, no one had kind of built a product like this.

2:01And when you went and talked to people in the industry, they said you couldn't and we didn't know how to believe them. And so decided to try to build an early version of the product without code, like in a spreadsheet for Segment, another YC company where we had some friends who are kind enough to let us sort of hang out in their office and interview their engineers and try to build this prototype. And I think they were both kind enough and they needed a SOC 2 and didn't know how to get it. Anyway, and so we spent two weeks in their office reading a bunch of SOC 2 reports and trying to standardize them.

2:31And then interviewing their team and kind of making them a roadmap to here's how you would go do that. And that was like the very first version of the product. And then for the second version, we took that spreadsheet literally to another YC company front. And sort of gave them segment spreadsheet but changed just a little bit to see if it worked for them. And that's how we tested if we could standardize what had previously been an ad hoc process. And it mostly worked. And were you super psyched when that happened? Yeah, kind of. Because you kind of didn't know whether it worked. You sort of like slide the link across the table.

3:06It's awesome, right? And now you're huge. Tell us how big you are. You're huge. Come on. It's a little. Yeah, we are 12 ,000 customers. We have 1 ,000 people who work at Vanta around the world. 1 ,000 people. Wow. Okay. That's wild. It's wild. And between now and when we taped for the Social Radars episode, you've raised around or you announced around. Yes, we announced around. We raised our Series D. Valuation was$4.15 billion. Get out. Oh, Christina. That's amazing. This is so exciting. I'm so excited for you. Yeah, me too. Okay, so you have gone from sliding that Excel spreadsheet across the table to raising your Series D.

3:49tell us things you've learned how you've grown as a manager and maybe what your experience with founder mode is what does it mean to you for me i think at the highest level founder mode is almost a like permission to run the company the way you want to run it and i think that's in part because the journey is very long um even when things work they're very hard uh and so if you kind of don't enjoy it along the way you just like it will not work or it will not work for many people probably myself included so you kind of have to like enjoy the journey or make the journey something you're you like jump out of bed for um and to me founder boat it's like you should figure that out to yourself and not do what you know like sandhill road vcs tell you to do which again may or may not work but if it doesn't work for you it's like not going to work for your company yeah did you ever have something that sandhill road people told you to do oh absolutely Can you give us an example?

4:50Yeah. Let me try to think of a good one. I mean, we had, so we, for various reasons, I think we talked on the podcast, waited until we had$10 million of revenue to raise a Series A. Yeah, I remember the story. Yes. And that was just weird. And I think, not just weird, but folks interpreted it as like a lack of ambition. Or like, oh, they don't want to build a venture-backed company, clearly. Oh, they're a lifestyle company. Yeah, exactly. Exactly, their lifestyle company. And you're like, oh, no, no, no, I'm going to be a big one. So they were approaching you, and when you said, no, we're not raising right now.

5:25We're like, too busy, we're set. Thank you. Yes, they'd say lifestyle business. Yeah. Interesting. Yeah, which I think as you can imagine, I was like kind of annoyed. And then I was like, oh, you think that? Great. Well, I look forward to like talking to you in a bit. Yes. Like just you wait. Have you ever been tempted to delegate to managers, not just because like you are, you know, this is a marathon. You've said it, you know, you're in it for the long haul. That's a marathon. You've been around for a long time now. But like if you delegate, maybe your life gets a little bit easier. So like how do you fight that on a day-to-day basis?

6:04That's a good question. I mean, I've definitely delegated stuff that worked and didn't and that I shouldn't have.

6:12okay so the trope is like pick your battles but i think the version of that is like i don't know the founder at least i am like kind of always annoyed when stuff doesn't work yeah um but where am i going to be really annoyed i guess and like where will i be sort of annoyed but then kind of understand and like can kind of move on and trying to know myself well enough and reflect on places there to figure out you know kind of what am i i really like won't be like totally okay with slipping but i can live with slipping versus like i will just be like upset at myself for having delegated that thing yeah yeah so it's just all about like picking like you said it's picking your battles yeah this is a marathon i have to delegate some things but i know myself well enough to know which ones i need to stay in founder mode for right yes yeah i feel like the concept of trusting your gut has come up everyone has their own take on founder mode but they all sort of say trust your gut right is there a story that you have where you felt something deeply and and followed through on that despite other people yeah and I can also give you the reverse yeah yeah do both yeah um the reverse was actually we lost like a very early and excellent engineer who's gone up and has it like has and will continue to have an incredible career um and we lost him because we put a manager over him.

7:31And like kind of knew, or in some ways I like, when I heard that plan, I knew it wouldn't work. Whose plan was it to put a manager over this person? Their manager. It was going to put someone in between. In between. And there's, you know, like you can, there's a, there's a, you know, Andy Grove would have told you to do this, right? Like it wasn't crazy at all. Okay. And I heard it and was like, oh shoot, that's not going to go well. I should do something about it. And then it's kind of like, and there's 17 other things and I'm a headless chicken. And then, you know, kind of the day we told this person, they took an interview and, like, ended up leaving.

8:04Wow. In a very kind and friendly and professional way. You know, but it's just actually something you could tell. Like, to this day, I still am, like, I am an idiot. And I knew that I was going to go badly. And I did not do anything about it. And, like, I do think Vanta is, you know, incrementally worse for that having happened years ago. Totally. Wow. Yeah. Like, you're still a little bit obsessed with it. Yeah. And, I mean, to be clear, like, I'm incorrect myself. But, like, yeah, totally. I should have caught that. Yeah. 100%. What about the reverse? Obviously, the$10 million, we know that's a great one.

8:33Yeah. Yeah, and I think both from a business outcome and I think actually it helped at the time. Again, the company kind of have more confidence in a way because it's like we're doing well because we think we're doing well. It's not like we're doing well because fancy VC says we're doing well. That's a nice bonus, but not – I don't know. That can come and go. Right. I think the other one or I guess another one is like launching additional products before the first one is done. Even in the vein of the first one, it's never done. But for Vanta, we sometimes talk about it as we didn't start to be a sock two factory.

9:16I'm kind of purposely pedantically calling it a sock two factory. and we didn't think a sock two factory would be a good business turns out it's actually a very good business um but still that's like not the plot and so underlying that is i think like maybe a professional manager would be like no it's actually a good business like and there's like lots of room on market and like just keep going and investing and like just do the thing but we kind of always thought like that's that's not why we're in this that's not why we've recruited people again like maybe good business, good financial outcome, but like not the game here.

9:48And so invested more consciously and larger and earlier on and just trying to get additional products working because we didn't want to be known for just that one thing. Being a sock factory. Exactly. Sock two factory. Yeah. Sock factory is a different business. Sock factory, like I don't know what it sounds like. I keep thinking about the story you just told about how you felt in your gut like you shouldn't put the manager over that person. You were too busy. I feel like if I look back on my career at Y Combinator, most of the biggest mistakes that I feel regretful about were, I think, because I was too busy.

10:26And I thought, oh, you know, I have other things to fight. And you just get distracted and you move on. And then all of a sudden it turns into this big problem. Is there any advice you have about balancing sort of being a founder who has a million things to do, listening to your gut and acting upon it when even when you're too busy? I mean, if I think of what I was kind of too busy doing, some of it was like calendar blocks of my time, but actually mostly it wasn't. It was like emotional energy. Right. And I was spending a lot of time in a part of the team that I mean, wasn't working, but like wasn't working in a way where it felt like we were like all in the boat together uh we were you know across across the shores like kind of pointing at each other and that was just like very draining for everyone involved um but i kind of look back on that and i think it's like okay well when you feel like you're in you know in the boat pointing at each other not in the same boat um fix that real quick because that is so draining uh like emotionally draining and then you don't have the fortitude for like the other stuff um i don't know that's helpful but that's kind of it's like less of a calendar I mean you've calendar problems those are easy to solve uh it's the like no I just need to lay down for a moment please or like I'm done thinking yeah yeah has your sense of like trusting your gut changed as you've grown to a thousand people have as you've done this for more years raised more money I think so and I think it's uh like hopefully it's getting better um but I think I'm more attuned to whether you're right or when you're right and you trust your gut great uh when you're wrong and you trust your gut hopefully you learn and like your gut gets better yeah if you're right and you didn't trust your gut i you did you did the thing you didn't want to do i don't know that is just like i get i get really angry at myself then and like that is i just kind of want to avoid that state i think and so it's almost like a version to that that will lead me to like trust my gut more if that makes it right where you're like i might be wrong but at least i will like then learn from it yeah versus i'll just be like wrong and bitter which is like not helpful to anyone you don't want to be wrong and bitter wrong and bitter it's just like not good well this was awesome I can't wait for this to air and if anyone has found this interesting they're going to be so psyched to hear your full Vanta journey because it was such a great episode and it should come out pretty soon too thank you so much for having me thanks Christina bye