From YC darling to fundraising powerhouse

By Jason Yeh
July 27, 2021
Listen on Apple Podcasts

From YC darling to fundraising powerhouse

For the three years between her graduation from Y Combinator to her splashy $50MM Series A raise from Sequoia, Christina Cacioppo and her company Vanta kept a low profile. Back in 2018, they had been working in a space few people were talking about around Silicon Valley. SOC2 compliance for startups hardly got people excited. Then, almost out of nowhere, came the announcement that Vanta had raised $50MM from Sequoia Capital. Christina shares how she got to this point and how much impact YC had on the process.

Episode Transcript

Christina: [00:00:04] I just basically blurted it out- "What do you like about Vanta?" What happened is they just went around in a circle and basically each said why they should do the investment. I wish it was like 3D chess, but it was like straight checkers.

Jason: [00:00:21] This is Funded, a show where founders who raised millions in venture capital share the gritty side of what it actually took to get that money in the bank.

I'm Jason Yeh. Not so long ago. I was trying to get my ideas funded. Back in the day, I was a VC listening to founders pitch me for money. Ah, YC- the Harvard of accelerators. 

Anonymous: [00:00:45] Y Combinator is looking for successful startups that can grow very quickly. 

And when you have YC in your bio, you instantly earn the respect with anyone wearing Allbirds or a Patagonia vest, which can be very valuable. 

They have seemingly figured out how to turn small ideas into large businesses. 

Jason: [00:01:05] Today's show is going to help you understand that golden reputation. Instead of talking about the shiny household names Y Combinator has backed, like Airbnb and Instacart, we're going to talk to a YC-backed founder who's on her way to the top. A few winters ago, Christina Cacioppo got the email that most founders dream of.

A message from Y Combinator saying she had been accepted into their three-month program that culminates in demo day, when investors show up in droves to hear pitches founders have been poring over for weeks.

The company she brought into YC is called Vanta. Vanta automates the process of getting and maintaining security certifications like SOC 2 and HIPAA compliance. Now with over 1000 customers and a fresh $50 million round led by Sequoia Capital, Christina remembers how valuable the rigor and accountability of YC was at the start of Vanta.

But more importantly, she shares with us how the program impacted her fundraising- from her raise coming out of the program to the relationships that would help close her series A. But first, let's start where we usually do- what she was like as a kid.

Christina: [00:02:23] I grew up in the Midwest in Columbus, Ohio, as the daughter of two professors who worked at Ohio State and loved their jobs. And so growing up, I thought everyone was a professor. It took me a while to realize that people did other things. And then the second bit was I thought actually everyone loved their jobs, and work was a fun thing that you didn't do all of the time certainly.

But when you did, it was generally good and could be frustrating and ways. I think I was actually just in retrospect, really lucky to have parents who loved what they did and what they did was research, for the most part. Research and teaching. 

Jason: [00:03:09] Okay. So in terms of like what you got into, and what you were interested in, did it foreshadow, the career that you would have, or did you think you would actually go into something more like academia? 

Christina: [00:03:20] Yeah. I thought it was going to be an academic until I was about 21. Like it's sort of joking, but I truly didn't realize people did other things with their lives until I was much older that I could too.

Yeah. That said I was also the kid who tried to have a babysitter's club by herself, but no one replied to my flyers or had a lemonade stand on a street that no one went on. At one point,  sold things, magazines door-to-door with slightly more success in those other things.

But not really. And so there is this kid with the lemonade stand story, but also no one came to my lemonade stand. So I don't want to index too heavily on that one. 

Jason: [00:04:01] Well, what you're probably not realizing is that you're talking about seeing a lot of failure early on and seemingly not being too phased by it.

But all jokes aside that does seem to be a characteristic that I see whether or not a founder is outgoing. It's more like really interested in tinkering, problem-solving and figuring things out, but we'll, we'll sort of fast forward here. You got into YC with an idea that, from what I can tell, came to you as you were at Dropbox, correct?

Can you, set the groundwork for your time at Dropbox and the decision to leave a big company that was scaling,  with probably a really good path ahead of you?  

Christina: [00:04:48] Yeah. So I joined Dropbox, in very late 2014 and was really fortunate to join what's now the Dropbox paper team. Fortunate in a lot of ways, one of which was it was a five or six-person team that sort of worked in the corner on this acquisition and turning Hackpad into what's now Dropbox paper. And so we thought of ourselves as the startup within a startup, a startup within Dropbox. And we had this new product we were trying to take to market. It was a collaborative document editor. That's now out of Dropbox paper. It was disconnected from the rest of Dropbox. Because again, we were building on this acquired startup's technology, and step one was, go get users.

And we hadn't been able to get anyone who didn't work at Dropbox to use it, which is like signal one of like, oh gosh, product-market fit- questionable at best. And so that was kind of what I said about doing, when I joined as a PM was like, ah, we'll figure out what to build, but I need user feedback. I, Christina, don't know how to build without it.

Yeah. So, in order to do that, did a few things. One like chased down everyone at Dropbox I could find, and it was like, Hey, does your roommate have a startup? Does your partner have a startup? Like, can we give them like this thing? Like, well, they try it out. And the joke that's only sort of a joke is like, I went sort of, I don't know, one for like 52 and that like talk to 52 people and we got AJ's mom to use it.

AJ was an engineer in the team. His mom was a wonderful mom, like in general, and had never used office 365 or Google docs. So she'd never used collaborative document editing. So she thought what we were making was like the best thing in the world. And then we introduced her to Google docs and then she liked that a little more.

Cause she's coming from Microsoft Word so it was not going so well. So then went to the account managers at Dropbox and were like, Hey, can I, can you like, basically pitch your startup customers and your growing startup customer found this new thing and we'll just give it to them. And the account managers were like, game on. This is great.

I just call up people and try to upsell them so good. I, meanwhile right. Had never worked at a company before. So like, I don't know. It seemed like a reasonable thing to do to me very quickly, not a reasonable thing to do when the legal team sort of chased me down and again, very reasonably and nicely.

We're like, we're voiding these contracts and you need to stop sort of like contracts. You have them. How novel. So one of the things that every one of the many things we were avoiding when these contracts were like, oh, Dropbox is SOC2 compliant and secure and pen tested and regularly audited.

And, you know, like just says in the contract, right. And we are, as much as we thought we were our own little island within the company, like still very much worked at Dropbox, so still had to uphold all of that. And so again, the lawyers were, actually reasonable and during their jobs. And we sort of had this decision as a product team of, we can either go fulfill all of these contractual obligations.

It'll probably take us a year and a half probably have to migrate to core Dropbox. We won't do any product development, by the way, we don't have product-market fit, or we can not do that. And go find our own customers. And that's what we did, which I think was hard to judge, but the shot and the score now. But what I mean was just really hard because at that point you're like, okay, you're the startup within the big company.

Right. But you actually don't get any of the big company resources. Right? Like you don't get the distribution, you don't get the go-to-market help. You're sort of again, on your own. And I think there was just kind of reflecting on that experience a bit of like, look even Dropbox scale and size and engineering prowess and all of these things.

It still takes a year and a half. Like, this is crazy. Like why it's so anyway. And so that's, that's where some of it started with trying to figure out why it would in fact take so long. 

Jason: [00:08:42] Right. And so I think the genesis of a startup idea is something that I look at when, when I'm, when I'm angel investing.

Certainly something that I looked at when I was a pure play venture capitalist. When I'm talking to founders about what does it mean to actually go out and get venture capitalists and professional investors to back you. I always kind of come back to that because I do want to know, like, what was the driving force behind the founder?

And is there going to be some level of like expertise or passion that just like drives them forward? And this is one of those interesting things. Like, I was very curious to hear this part of the story because you are, and you can correct me if I'm wrong, but by the way you describe it, you certainly were engaged with the problem.

But it was, it was like, you were identifying your problem. You weren't like living that all the time, but you decide that it isn't like an interesting enough product right to apply to YC. But I wonder if you could say like a few words about like, you know, bring yourself back to this idea of like, I'm going to jump from gigantic Dropbox actually doing this business because I saw a small problem.

Christina: [00:09:58] Yeah. 

A few thoughts. So one, I very much wanted to do a startup and joined Dropbox again, for a lot of reasons, there was very much a thread of, I want to leave. I want to start something. I am in ways that are helpful and not helpful at all, skeptical about a lot of ideas. I have a very high bar and I think some of it's a personality thing and some of it's having worked in venture.

And so this would be hard, but that was always the ultimate goal. I think also actually having done this somewhat before, as in left venture, didn't have a job, tried to start a company didn't quite work, having gone through that and being like, okay, worst case here is I get a job at Dropbox, right? Like I am extraordinarily privileged and it will be fine.

We can talk about what gradation of fine I want to fall on. But like, this is, this is okay. So I think there's like that bit, which I just believed, I sort of intellectually believed the first time. And then like deeply viscerally felt the second, right? Like the worst case outcome again is I'm going to be disappointed with myself, not anything else.

So all of that. And then do the actual idea. So it was not as much of a light bulb moment at Dropbox. Like this is the way the founding story meets reality. Like all of that happened, but I did not sit there and be like, aha then yes, she'll make it automated security and compliance startup.

Like that didn't happen. It was leaving. Having a bit more head space to think about things and looking around and being like, and this was late 2016, early 2017. And so it's to take you back there, it's the 2016 election and everyone's emails everywhere. It was Equifax and sort of looking at and being like we say, security on the internet is so important.

And yet we are so bad at it. And like, why like get that we say it's important and we spend time on it, get that we say it's not important that don't spend time on it and bad things happen, but like what is going on? And so actually a lot of 2017 was starting with the initial conversations with the Dropbox security team and moving up to like eventually kind of building the MVP of what is now Vanta.


Jason: [00:12:13] So what does an MVP, a minimum viable product that gets backed by YC look like more than that after the break.

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Everyone wants to know what it takes to get into Y Combinator. The story goes that Airbnb got into YC with a cereal box of something they called Obama O's longer story. Christina. Her MVP was a little less sensational.

Christina: [00:13:56] Going in, had done a bunch of prototyping, had a really early product that one early customer called a brutalist white website.

I think went into YC with, I think a bit like whole lot to do and show and all of that. But I think the underpinnings of being like, okay, there's a there, there, right? Like again, a lot of work, but we just had five people who granted were friends, but all who said, I would give you thousands of dollars for this thing.

And so at that point you're like, okay, you're not just being nice to me. Like there's, there's something here again. So I think just emotionally and like kind of managing on psychology, like that was really helpful. Is it also just made these things seem more attractive? Yeah. 

Jason: [00:14:51] Got it, got it. That would love to hear what else you saw because like we're going to lead into describing what it meant to them.

Gotten raised off the back of that. 

Christina: [00:15:00] Yeah. I think the other part is the feedback I got when I worked in venture from one of the partners at USP who has a famous blog was, he was at some point and I was trying to figure what I was doing with my life. One of the things he said to me was you are not a fake it till you make it person.

And you can either like, decide to be one of those, or you just need to like put your head down and do the work. But like, you don't try to be that person basically without it, which actually was actually pretty helpful. And in the intervening whatever eight years sense, like, yeah, I'm just like not a fake it till you make it person.

And so part of YC was being like, okay, Maybe in theory could raise off of like shiny background or like having worked with these people, when I was in venture and they were in venture, but I don't want to be that person, like that will make me very uncomfortable and unhappy and sort of unhinged in its own way.

And so like, we just got to have real results. And again, we definitely helps, but was very much of the mindset of like, I should not coast on these things. Like I should coast or like we should be raising on the backs of like customer traction or revenue traction. And that's very much the filtered into Vanta to this day.

Jason: [00:16:17] I would love for you to talk a little bit about the fundraising process that happens out of YC. And maybe you can talk about the culmination of YC and demo day. Like, let's start there, maybe talk through that. 

Christina: [00:16:27] Such an impressive thing. So it's. So like, it is such a, like a mastercraft and I don't know, design in that I remember.

So I got to go to demo days when I was at USV. Yeah. And I remember like, this was the era of like Paul Graham standing up in front of everyone and being like, Airbnb is in this batch somewhere. I don't know what startup it is, but that's your job. You will find it to like, let, let demo day begin. And he was just like such an incredible master of ceremonies.

And I think again, like design pieces, like constructing that atmosphere where you're like, there's good stuff here. There might also be stuff where we're going to make fun of today or in five years or whatever that won't work out. But the like actually strain of optimism through that, it was just like really well done and was still very much true, whatever, 10 years later when I went through like kind of differently, but they do a really good job of supporting founders and then the run-up to demo day kind of being like, this is about you, this is not about investors it's about your business.

And then immediately after demo day, turning around and being like, okay, look, you guys have not won yet. And if you are on a high horse, like you were going to crash down in a month. And so like, we're just going to tell you that. And some of you will listen and some of you won't, but like, let's go and let's tell you some stories of startups that were like doing so well and then went through the trough of despair and then pulled themselves out of it or, or died.

So I think they actually do that really well. And also that's not that stuff doesn't get the TechCrunch headlines, but there is this like post briefing of founders of being like, and now the real work starts just, just in case anyone was not clear about that fact. The other thing I think they're actually remarkably good at to this day is in some cases, understanding a business's potential more than the founders.

I think it's the perspective, both of just like not being deep in the muck and also seeing so many startups, but being able to like pop up a few levels and being like, yeah, you're saying XYZ, but actually you're actually doing ABC. And when they say this it's again, it's not used car salesman or like charlatans, like they believe it.

And I actually have this amazing video of Jeff Ralston being like noted to me being like, you shouldn't be thinking this, this is a Vanta to pitch like dah, dah, dah, dah. And his pitch was just so much better than mine. Right. And it's like, embarrassed. It's embarrassing at the time. It's embarrassing now. Cause you're like kind of had been doing it for like six or nine months slaved over that pitch.

And Jeff just like, sort of walks up and it's like, no, no, no, not that this and he was totally right. And so whatever that thing is, like, they're just really good at it. 

Jason: [00:19:04] Yeah, no, let me summarize the first two things that I've heard. They're really good at understanding what the big story is, right. Like, okay.

Yeah. You keep saying you're doing compliance, but like compliance is just the first thing in terms of the actual iceberg that you're you're tackling. And so I think like they know that they know the psychology of investors very, very well, and they've seen the stories that hit and they invested in the gigantic stories.

So they can, they're really good at helping craft the story, which again, and when you're fundraising is the product, right, it's the story that you're selling. And then that magic craft you talked about, which is like creating the set of circumstances and the alignment to push a process that creates this feeding frenzy.

And like that has been something that people have tried to recreate.  I don't think anyone has really come close to that, but, um, and I think those first two things just can't be underrepresented in terms of the value of what happens in YC based fundraising. Is there anything else that you think we've missed in terms of pushing this.

Christina: [00:20:17] I think one of the underrated innovations in Silicon valley and startups is the safe, like Carolyn Levy and YC just do not get enough credit for standardizing what, again, when I was at USV was like a bespoke process and negotiation and took a lot of time and then the founder would be like, well, I have this equity term sheet here and this debt one here.

How do I weigh these? And like Carolyn and the YC team just like standardized that whole thing. And now we, now the world runs on safes and it's infinity more efficient and yeah, it's just like, now it's accepted as a given. 

Jason: [00:20:55] Right. And, and I think like the component I would extract out of there is speed.

Right? Speed. Get the, it gets these deals done. And by removing the friction, they're just adding speed to the process, which is a great call out. Maybe now we can talk more specifically about vanta I'd love if you kind of, you did. Can you remember the story you told, at YC demo day and you know how you went out there?

Christina: [00:21:21] Yes. So we were automated security and compliance starting with SOC2, right back back then. I don't know if we put schlep business on the slide we may have, but yeah, somebody at YC, Dennis, very good at pitching, sort of tried to explain the business a few times and it only sort of worked. And then the person was like, oh wait, you are something that everyone needs and no one wants to do.

Got it. I get it. So I think actually we did have some sort of slide like that. The biggest question we got was around market size. How big is this? Which is kind of funny now having watched how much this space has transformed in the last few years, but at the time it was just like, no one gets soc2.

It's like what you want to sell soc2 to the startups? Like, what are you talking about? Like, again, seems smart, shiny background, but like this doesn't actually make it. 

Jason: [00:22:09] What was, what was your take on it? 

I hate market-sized questions. I just asked do 

I, as do I, so I'm actually, I hate, I'm actually curious at how you thought about it and whether you tried to convince, or you just said, look, you either believe this, or you don't. 

Christina: [00:22:25] More the latter.

So like I kept trying to drop the slide, and like Adore, a group partner. So good. Adore would be like, you need to put this in. You need to put this in I keep trying to take it out. I think, I think there's like something very hand wavy in it where he ended up and I didn't fit in longer conversations.

It was like, look, if you want me to count up how many SOC2 are in the world, I'd actually done this exercise. It was like, you, like, this is like, this is not what you should be thinking about. Like, right. This is a bet on, do we trust the security of software? And are we concerned about that today?

What's your answer? Cool. Okay. Are we going to be more concerned in the future or less concerned? More. Cool. Okay. Let me tell you how we reason about this today. We reason about it with like accountants and auditors checking screenshots once a year. Do you feel good about this or less? Good. Great. For someone going to fix it?

Yeah. Okay. How about us? You know what I was like, kind of like trying to first principles them into anything and be like, don't just don't count up the number of SOC twos, because I think we did that and it was like, not very many, many more today. It was enough where as much as I hate the market size question and it was trying not to answer it and hopefully an elegant way.

It's very much something we thought about internally because we were like, well, shoot, if there's only 2000 of these things in the world, like that's not very many customers. The thing we found since then is like dropping the cost, like both the macro trends and all the first ones stuff has panned out.

And when you drop the cost. You get a lot more of this behavior. And so like, we have not eaten up half of our market size in two years. Turns out it's great. But yeah, they weren't totally crazy questions. 

Jason: [00:24:03] Yeah. Maybe you and I having been ex venture capitalists and maybe you were with some angel investing as well.

Like why don't we talk about why we hate market sensitivity questions? I'll let you go first. I'd love to hear how you think about market sizing and what frustrates you about that stereotypical question that comes out. 

Christina: [00:24:23] Yeah, so I think, right, like I grew up in union square ventures in the age of large networks of engaged users and like the four square, I think series a got signed the day before I started.

Right. Just to like date it. Right. And so it's like, what is the market size for like a check-in app? And you're like, Nah, I don't know. Right. Like this is just totally what is the market size for a tweet, right. Yeah. And so I just grew up in an environment where those questions were so absurd that they didn't get asked.

And if they got asked you would get funny looks, right. It was just much more of a, like, what is the human behavior driving the thing, like why would someone broadcast to their friends that they're, they're at the taco store on the corner. Okay, cool. Like, do other people share that?

And so I think there's definitely a part there where just for these new behaviors, it was just a, it was much more of a first principles thing there too. So I think that's part of it. Yeah. What about for you? 

Jason: [00:25:18] Yeah, for me, that's certainly some of it. I've just been, always interested in backing people with big, big ideas and big visions where I believed, like if they had a narrow point of view or if they were focused on something specific, they would create

touchpoints and relationships with customers that would just expand their vision. And I was like, I would actually rather them be able to be focused and like land with a customer and started start developing that relationship and problem solving. And knowing that if we back the right founder, they would be actively looking for tangential markets or how to grow the market.

That was probably something we didn't worry about. Like if they were going down in a direction that was limiting, they would have had created such a great relationship that would give them feedback around. Okay. What's the next thing that we add on to, and if I had to oversimplify, it's like not being defensive, but just being ultra confident in, in the problem, right?

Like the, the connection to the customer and their problem. And I'm essentially giving the opportunity for you to land and grow. 

Christina: [00:26:27] And like a bit of, I think on the piece of just like for folks are very much convincing myself, at least like people who didn't buy into that would not be helpful investors.

And like, that's not in a, like, they'd be malicious just in a, like, they'd be just confused. Right. They'd be like, confused about a lot of things. And so also looking at that as like filter criteria of like, look, do you want to like, believe in this vision and like go on this journey, skipping into the sunset.

And like, if you don't totally reasonable, got you. Like, we shouldn't skip into the sunset. Great. But looking at it that way too. 

Jason: [00:27:02] No, I, I think that's really important. I think that's something that I encourage founders around all the time. One thing I kind of wanted to also spend time on is like SOC two compliance, especially back when you started wouldn't have been something that a lot of people saw, right.

Not at all. Right. And so like the story you tell had to be very compelling in a certain way. I talked about this in that actually a previous interview, but there's this idea that I always come up with around narratives, which I call believer, matching, like I believe your matching framework. And that is to say that you probably had an idea of a, a archetype of an investor who, if you found that investor, that investor would get it, but in the believer matching framework, I will say, okay, great.

You know what that investor looks like now, what, what do they know that other investors don't know take, you got to take that out and still that, and then try to spoonfeed everyone so that they can get up to speed very quickly. Do you, do you have a sense for like what worked and who were you able to convince.

Christina: [00:28:09] Interesting. So there probably is something to the former operator piece. The thing that did like more salient in my memory similar, but his investor who has sat through board meetings that are like, should we do SOC two, it's a board level issue. Like, should we blow up the roadmap for two quarters to like, you know, those people were like, I, yeah, I know.

Remember those board meetings, right? Like if you have the magic pill, if you have the cheat code for this like game on, like, do you have the cheat code for this? Right. Anyway. And they tended to be, those were very different conversations to this. Cause they were like, oh, I don't think there's a cheat code.

Right. Like, prove like, what does your product actually do? And how does this work? Because this world is so bespoke. And then this is where we're like, right. It has been bespoke. Let's talk about why it is and let's talk why security practices should actually be pretty standardized. So you know what we've done, or like productized is like 90%, the same 10% change on the edges.

But like, this is actually the way it should be done. And to that, you know, anyway, so we have just like a very different conversation than the, like, I haven't heard of any company smaller than Workday getting a SOC two and here you're telling me you're going to SOC two. So by like, what are you like? What, like, what are you talking about?

Jason: [00:29:23] Yeah, no, that, that makes, that makes total sense. So a lot of times you'll see companies come out of YC, raise big rounds, and then shortly thereafter, like six to 12 months later, there's just a momentum to like, do more and you hear more about them and there's this like raise more Vanta on the other hand, kind of did the opposite, right?

We looked for a little bit more of digital exhaust around Banta between 2018 and 21. And you kind of. Disappear. We'd love to hear a little bit about what those years were like for you. And, and, you know, if there is a, an overt strategy or what you were doing. 

Christina: [00:30:08] Yeah. There wasn't a root strategy. So in the beginning look like, and by beginning, I mean, like, you know, after YC summer 2018, that was just like, oh, we just raised all this money and it's still just two founders.

Like, let's go recruit engineers in particular. So then it was a bit of like, okay, shoot. Now we want to go soc2 everyone, but we've never actually soc2'd anyone, so let's make sure we can do it before we go tell everybody we can. Then we got a little more comfortable. There's a bunch of word of mouth.

And so it became, so the quietness was all like continued to be a strategy and it was twofold. One was, oh, this is actually a really good business and we can do it. And everyone still thinks for toiling in some random corner working on like this niche compliance thing. And so just like a heads down, go, like, we don't want this to become a hot space.

We do not want, you know, like, please think we're doofuses in the corner. Yeah. Cause we actually know like, this is, there's a thing here. Like this is working. And then the second part kind of, as it started working and you get that growth that has just like absurdly difficult prioritization where you're like, right.

Like when you have more customers and you're expected, no one feels sorry for you Nor, should they? Right. But you're sort of like, ah, shoot. Now we've got to like work at this scale. Yeah. And so like putting up a website or go and doing imp press was just something that, I mean, joking, but not like, I felt totally remit.

I was like, that'd be a terrible use of time. Like we have like, you know, kind of again, we're customers and we expected, like, that's the problem. And that focus took us really like kind of both sides, like took us really far. Yeah. Eventually like things started to change in that, like despite our best efforts, some word of our success did get out.

And so there were a few more kind of copycats and knockoffs. You're like, oh wait, wait, wait, no, no, no. Like we're here. Like hello. These things are not all the same size. Like there is fantasy. And so think a little more like, oh wait, nevermind wait. Still here. Yeah. Yeah. The corridor, 

Jason: [00:32:16] I think like your, by the way, like, I think you did something that can be hard to do, which is, like you said, like raising the money is only the first step.

Now you gotta like really prove that it's there and then don't put the cart ahead of the horse necessarily. So you go and prove that you can get it done and then start selling. So I just wanted to put a bow on that.  I think that feeling of prioritization being the real challenge is, is amazing, right?

Like the fact that you could say. We don't want to redo the website, which is a, I forget what the phrase is. Oh my God. 

Christina: [00:32:51] It's so janky. If you internet archives, it's like written in times new roman and it's like vanta. 

Jason: [00:32:57] But what a great signal, what a great signal is like. Yeah. Like we looked at our priority list and it's not even close to the top and what a great signal.

So let's transition to kind of this realization that look you could, you could have just kept going and right. Build this monster business on the backs of customer funding, but the environment changed. In fact, like, you know, it's interesting, like I kind of want you to talk about this look 2020, that, that, that must've been it right.

There is a really interesting set of things going on. Obviously COVID right. So COVID is happening. And then there are like two or three startups who must've been raising at a similar time, or maybe they raise and you saw it. You're like, oh, what's this like three to $4 million fundings that look like a very different story.

Can you paint the picture of 2020 and kind of what's going through your head and, and w what the trigger point was to, like you said, raise your hand and say like, wait a second. Like, maybe we will go get some money. Yeah. 

Christina: [00:33:58] 2020, what to say about it? So, okay. Banjo wise, we started the year at 15 people and about 200 customers.

We ended at about 45 people, employees and 800 customers. 

Jason: [00:34:13] Say, what was that number? 

Christina: [00:34:15] 800 Customers in 45 people. Wow. Just a lot of growth cross the board, just like there were like five Vantas in 2020 joking kind of not. And so you get all the good of that and all of the pain of that, right?

Like whatever process or, you know, structure. Whatever you set up was like immediately obliterated, you know, and sometimes this was an exciting obliteration and sometimes it was like, come on. And the analogy I started using is like, Vanta, it's just this like giant treadmill. Right. And we're all running as fast as we can to catch up, to keep fighting the treadmill.

And everyone gets turned off the back sometimes. Right. And like, you just gotta like get back up. It'd be like, right. Well, anyway, it's like 7.4 gotta be pace. One of the hardest parts are right when, when somebody or. Anyone gets thrown off a treadmill, a bunch. They like, at some point, get angry with the treadmill.

They don't get angry, you know? And so just like all of that. And then all of that in the backdrop, like all of that fast growth in the backdrop, but like, and everyone has a zoom square and no one left their house in three months was just a lot general for everyone. But just to say 2020 was a lot. So all of that said, you know, the goal has always been to build a very large internet business and the, you know, company mission is secure the internet.

That's, it's, don't actually mean that in a tongue in cheek flippant way, it's like, oh yeah, what's the scale internet scale. That's the scale. And so, the lifestyle business, that we were funding and off of revenue was in some ways, just a happy accident of realizing early on we could charge annually upfront and then being like, well, this is great, right?

Like now we understand cashflow deeply in a way I get I'd read the Medium post, but didn't actually understand. But I think one of the two things, one of the things I started noticing was some of the investment decisions were just like harder than they should be. Right. It's like, oh, can we spend six figures advertising on like a really big podcast?

Right. And it would be like, ah, yes, probably. And it's fine. But also, you know, the bank balance and dah, dah, dah, and it was just like the answer to this should be us and the whatever 27 minutes we spent talking about it, like should have been used for something else. And the other bit too was just, there's some metrics that proper CFOs will tell you if like how many months.

Of cash of like payroll you should have in the bank at any one point. Yeah. And as we were growing and our bank balance was staying basically flat, like we were just shrinking on that number and there was never a point where it's like, oh gosh, are we going to make payroll? But I did sometimes have these thoughts of like, man, if something happened and Vanta went under, because I was just like too stubborn to put $5 million in a bank account, I would just feel like a fool.

Right? Like that would just be dumb. Like it's wonderful that I'm, you know, skating on this edge, but like, I don't need to be anywhere near this edge. And also now there's all these other people at stake. And so we like should not be playing these ego games. 

Jason: [00:37:18] Yeah. And like, to just put this into context and I'm taking this from one of your announcements, we're talking to the scale of like $10 million of ARR.

Like this is not a small business at this point. And so you went from. Raising $3 million, not knowing if you could actually perform the service that you wanted to build a business off of.

to, $10 million of ARR, which is an incredible achievement, but as you go out and you think about these things and these all make sense to me, right? Like the, the speed of decision making of, of not, you know, not having to be perfect, right. To make the decision and go like capital for that fantastic idea.

And then also just like a war, chest and padding so that you can weather storms and, and be a little bit looser as you go forward. Totally makes sense. So at some point you're like your CFO probably had been probably yelling at you for a while. Right. Which is like, I guess the other person on your, 

Christina: [00:38:21] I wouldn't recommend that by the way, 

Jason: [00:38:25] a hypothetical, maybe a board member, finally gets to you.

And there is this idea that you're going to go raise money. How did you think about the strategy of raising money? And we'll, we'll sort of, I think I'll just give the punchline, which is you raised $50 million from Sequoia. I've never heard of them, but I think they're fairly reputable firm, but there's a little bit back there's, there's a little bit between there that, um, you would love to hear about.

So like you knew you wanted to go raise money. How did you think about it? You'd been a venture capitalist before you'd raise some money before. I'd love to hear about that whole decision matrix. 

Christina: [00:39:07] Yeah, for sure. So, and I think 2011, Marc Seuster wrote a blog post. This is something like formative VC days, couple lines investing in lines, not dots.

If you remember this. 

Jason: [00:39:19] I've referenced it a lot in this podcast.  

Christina: [00:39:21] It's very good, so good and so easy to miss. And so a few things, so. Raised our seed round from seed funds on purpose, because we're going to do the like raise in five days, YC thing. And didn't want to like implicitly choose a board member.

But as soon as that close went around and then had meetings with the VCs and sort of did the like, ah, shit, you know, we've just raised, but like so nice to meet, it's like 

a staying in touch thing. 

Yeah. And then sort of starting with that, over the next two years, it's built relationships with a few folks. One of the primary ways I did it was asking for customers, asking for customer referrals or which everyone does, but also pitching it to them as like, Hey, I mean, if you know of anyone, let me know.

Obviously I would like that, but you like, they're going to go through our sales process. They're going to do an evaluation. They're going to like maybe use a product. Diligence us go to town, like do all the things. Yeah. Kind of like positioning it as like, yeah, this is a two way street. And like, yeah, I get it.

We're going to say that out loud. And that worked really well really well from a customer acquisition standpoint. But I mean also from a, like, these folks knew our business really well. Right. And like much better than I even expected some of them to after this honestly, but it's just because they've talked to like 10 customers in their board meetings, right?

Yeah. So, yeah. I mean, I think like a lot of like cheat codes, like this cheat code starts with like step one, rewind two years. Sure. But, but that was a big part of it. 

Jason: [00:40:56] I think, you know, when you think about the process that you did finally run, I do love this asking investors for business development intros.

Like I, I think that is, you know, there are many variations on this and how you can get on VC's radars in the best possible way. Like when you're not begging for money, like it's the best possible time for them to discover you. There's a bit of psychology that I share with founders, which is like how powerful it is to make a VC feel like they caught a deal.

Like if they can feel like, oh gosh, like Vanta, you know, was, was out hunting for deals and just wanting to get contacted. And I wanted it connected to my portfolio companies and that's how I learned how they were doing like that feeling like whew I don't know if anyone else knows about this. Like, this is a deal I want to do is so powerful.

And I would encourage people to really think about that first principle and in terms of strategies for contacting VCs. So I see this a lot and founders who are great fundraisers, who had been in the buying position of a VC. So let's talk about it. You, I think you had a pretty exacting strategy, like you wanted to get something done.

Let's see how that went. 

Christina: [00:42:09] So if you felt so one had a overly complicated, like 12 attribute, like matrix of like, here's the things I want, you know, rubric or like, here's the things I want this person to have made that over the holidays when I had a bit more Headspace. And then when a month and a half later I was talking through it with a friend and it was like, his friend was also like 12 things, Christina, are you serious?

And you're like, ya, sorry. Only three matters. Like, let me go hide all the other roads of my spreadsheet. So maybe here, it was like, figure out what you want ahead of time. And then drop 70% of it kind of actually, or at least if you're me, like you've over done it until you need to drop 70% of it had that upfront though, which again, I think was helpful for me at least, and then email five or six people.

And it was just like, Hey, thinking of raising, or like got a raise would love to talk to you end of this week. Not pinging, very many people do not want everyone to know. Please keep this to yourself. Thank you so much. Can we schedule and then just went in and had those meetings basically. And with it had this timeline of like, hi, you know, it's very YC, but hi, you know, I'm having meetings from the state to this date.

I'm like looking forward to, you know, offers on this date. And then I want to make a, you know, a decision by this date. Right. I mean, YC helps, but I think this is just generally true is if you can keep saying like that scheduling or like that with a straight face. People might believe you it's you just got to keep saying it with a straight face.

And then you can conjure that schedule into reality. That's also a little like, well guys, I made this up. 

Jason: [00:43:48] Yeah, this is really interesting because people might listen to what you're saying. And you're like, well, yeah, but like Christina had 10 million in ARR and she's obviously she's going to be able to raise, I am just starting out.

Right. Like I just have this idea, but it, it doesn't matter. It's it's the same. And this is why I think it's the same, because it's conjuring and you're in, you're reaching no matter what, right. Because you might have 10 million of ARR, but you're going after a big round. Right. And so like, it was for someone to bet on you, it's just a later stage deal and they have to believe that you have another 10 X in you at least.

Right. And that is not any market style, investing, everything everyone knows is baked in. And so it could go either direction. And so that's what founders really need to realize about that, about the story. Yeah, done to perfection, great numbers. You were really executing, but at any raise, you are convincing people of one of two directions, which if you are, if you're going after the right valuation, it could go either way.

So, you know, I I'd love for you to talk about that. I mean, did you, did you feel like you had the price in mind or, or like, was it, was it at the end of the day you were going after five? Not everyone is going to believe that either. Like how did that feel? 

Christina: [00:45:12] Yeah. Built in some fuzziness. So went out and said, Hey, raising X to Y million for A, to B percent of the company.

So that actually put a really wide range on things. And with like, let me know what you think. And folks came in higher than I expected, but again, sort of the, like did not want you to your point, like pre-commit into like, okay, 400 or bust or, you know, whatever. Right. Cause like that's just not reality.

You go aside. So anyway, so went out with a range and then people, of course they're like, oh yes, that is a range on your slide. Like, how do you think about that range? And you're like,

I don't want to anchor you 

Jason: [00:45:52] anchor.

Christina: [00:45:53] Exactly. As politely 

Jason: [00:45:54] as possible. 

Christina: [00:45:57] I mean, investors in particular, I think it's also, we're saying their job on some level is to have those conversations just generally not a founder's job to have these conversations. So they're better at them than you are, or like they're better at them than I am at least.

And so like, that was actually helpful for me to be like, no, we're not going to answer my question. We're going to like laugh and divert. And like we're all gonna know him laughing and diverting and it's fine.

Jason: [00:46:24] It's fine. It's fine. These valuation conversations are going to fine, right. I think every founder who has raised has had that freak out moment, when we come back, what was able to convince Christina that it really was fine.

You already know this, but this podcast is just one of the ways I try to help founders better prepare to fundraise. Aside from hopefully being fun and entertaining storylines in our interviews on funded are meant to inspire and provide real life models for founders to follow. But a lot of listeners are hungry for more and write in looking for answers to specific fundraising questions.

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There's a saying in fundraising, you only need one yes. And it's not always about taking the first. Yes. In fact, the first yes. Can give you the confidence to keep going.

Christina: [00:48:12] I remember distinctly when we got our first. Yes, it was like a Saturday night. We got a term sheet over email and I remember just being so real and it wasn't a term sheet we ended up taking when I particularly wanted to take at the time. But I remember just being like, I didn't screw it up. Like there will be something great.

Like again, worst case. Totally great. Fine. Everything else. Wonderful. And over that yet, just distinctly on the seed round this time, it was so easy. It was just, you know, same emotion, but just a shorter cycle in that I got really positive feedback to the pitch. And so then you're like, okay, I don't know how, like, who it's going to be, what the numbers are going to be, how it's going to turn out, but like, someone's going to give us money.

We're cool. Great. And so it was just much shorter this time to begin. It was like feedback during the pitch. And I think specifically with us, I mean two things, one, because we'd been so quiet, kind of knew and knew how big we were and the guests range from like 1 to 8 million for the most part. And you're like, oh, no bigger than all of those.

That was in revenue. That was what I think, like it actually kind of gave me a, I don't know, the upper hand in the conversation, but it was that aprtright. Is having to your point in for two years, lived in like Vanta land and like Vanta's metrics are Vanta's metrics. And like, I mean, I kinda know SaaS baselines, but only kind of as I just didn't know what the outliers were.

Right. Like new things overall were good of course, but like didn't know kind of how good some of them were. And so that feedback was actually just also helpful calibration too. And I learned to ask people for that too, which was both learning and a little bit of a commitment device because you end up asking them what you're actually asking them is to say why they like your business out loud.

Yeah. It's actually a really good cause I tell them. 

Jason: [00:50:09] Tell me more about this. I was just about to ask you about very specific tactical tips and maybe this is one of them. 

Christina: [00:50:15] Okay. So when I discovered this is really first discovered in the seed round, literally was me with the seed firm. They were good. You know, you get to the, and he was like, I'd met with one partner and this was a full partnership.

And like, I knew them and I knew the firm anyway, but you get to the point where they're like, add any questions for us. I had nothing. I didn't want to be like, no, I'm good. Thank you. Moving on. Right. Cause he'd be like, don't want to do you feel like a doofus? And so I just like, basically blurted out, like, what do you like about Vanta?

He did not know what to say. Wow. It was amazing. What happened is they just went around in a circle and basically each said, why they should do the investment. And then they heard each other say it. 

Jason: [00:50:57] It's also really brilliant because it's a power dynamic shift where it makes it feel like, Hey, like we kind of know that we have other opportunities.

So tell us why you like us. 

Christina: [00:51:10] I wish to get over again. I wish it was like 3d chess, but he was like straight checkers. 

Jason: [00:51:16] It was like, dang it. I'm supposed to have that question written down. What is the question? Wow. That's a really, I had not heard that one before. I love that. I know. And like, you know, it is funny, especially when I talk to founders about how to raise money.

There are these things that you talk about that are like, oh, Strategies around fundraising, but it turns out like the things that you do just for fundraising sake have a lot of value outside of them. Right? Like for instance, like when I say like, oh, you really have to have this like passion for your business when you're talking, like people want to hear it.

Like, I am kind of telling you to put passionate and business, but I'm also just telling you, you got to have passion for your business full stop. And like, this one is very interesting. It's like ask the question because it puts them on their back feet and like, you know, makes them feel like they need to sell in, but you also kind of, that's a great question.

I actually just like, yeah, 


Christina: [00:52:07] in this bubble, like what's interesting about the bubble. I can't see outside of it

Jason: [00:52:17] in season one, my producer, Olivia Rheingold was just learning the basics around fundraising and different sources of capital in today's debrief. She leveled up and learned the hallmarks of a good accelerator and what makes YC so special.

Olivia: [00:52:34] Okay. Okay. So, okay. 

So my first question for you is, tell me a little bit about the reputation of YC within the industry. 

Jason: [00:52:45] YC is one of the most celebrated if not the most celebrated accelerator program ever created, essentially. Wow. Okay. I don't think that's hyperbole. It's really, really well-respected and it's not just the talk.

It is the walk in terms of the. Incredibly long list of decacorns, like, you know, multi-billion dollar valuation companies that have come out of YC, everything from Instacart Stripe, Coinbase, DoorDash, just like the who's who of the startup world have all come through YC. And I think that's important for you to know, just in terms of what the reputation of YC is, but that reputation has such a large impact on companies coming out of YC's ability to fundraise, because all that storytelling, we talk about all of the excitement from

investors, that's all baked in to any company that's coming out, them coming out of YC. And so investors just trip over themselves to try to fund almost any company that comes out of the accelerator program. 

Christina: [00:53:53] Okay. Gotcha. And it sounds like if you get accepted to YC, it's like an automatic yes. But do people ask you a lot, like I'm thinking about, you know, applying for an accelerator, like, is it something you suggest for people?

Jason: [00:54:08] Yeah. I do get asked about it a lot. I think some people actually infamously in my own, in my own history, in my last startup, we were recommended to go to YC and I was like, oh, I don't need it. Because I was like, well, the only value is really like, you get these huge valuations coming into YC.

And I think I can do it on my own, but it turns out yC is incredibly valuable for a lot of different reasons. The rigor that they put you through in order to learn how to grow a company, um, the network that they plug you into other companies that are all the same sort of the same age in terms of how long they've been around and supporting each other.

And then of course the lift around fundraising, it's all baked into an experience around being in YC. So you're right. The answer to YC is a hundred percent. If you can go, you should go. And other accelerator programs, I get asked about that as well. I think accelerator programs are really fantastic when it comes to

providing support, especially for first time founders. But I think that they can range in terms of quality. 

Olivia: [00:55:17] What are the questions you would tell those people to look for? Like, okay, I'm making this up because I don't know what I'm talking about, but for example, would you tell people, look at the history of the accelerator, like what kind of valuations people get coming out of it or what kind of just that's a made up thing, but how should people be evaluating these things?

Jason: [00:55:39] You know, I feel like there's been a lot of osmosis learning. And so the, the question you made a good point, I honestly, yeah. I think part of going through and accelerator program is, are they good at getting their companies funded and what does being good at that look like? So sometimes it's the valuations that their companies they're graduating companies get when they get funded, it's often they get funded.

And then I think the, the most important thing, or the easiest way to get a really good sense is to talk to other companies that have graduated from the programming and get their feedback. So was the accelerator great at supporting, their pursuit of product-market fit, were they great at supporting the fundraise coming out of the program?

All those get baked into just a very easy conversation with as many alumni as you can and say, like, what was your experience. 

Olivia: [00:56:32] Okay. Okay, cool. And so it seems like the program culminates in something called demo day, does every accelerator have a day like that at the end of the program? 

Jason: [00:56:46] Say generally speaking, yes.

Demo days is a really great way to essentially create the set of circumstances that make a fundraise happen faster. So why C and other accelerators get to essentially invite a ton of investors to all come to the table all at once, all looking at their deals. And so it is very apparent that a lot of investors are looking at these deals, which means investors are putting in this situation where if a company coming in, coming out of an accelerator program says, Hey, you know, we have a lot of, a lot of firms looking at us right now and they want to do the deal.

Do you want to do the deal that all becomes generally the truth, they could be making up whether or not a lot of investors were actually excited about the company, but the fact of the matter is there were 50 investors at this demo day. And so there probably is some sort of level of interest. So the demo days are really a great way to kick off fundraising for all of their companies, which is why it's done.

Olivia: [00:57:49] Okay. Gotcha. And so one thing that Christina talked about is that I guess at demo day, or just throughout the larger fundraising process, lots of people asked her about market size and okay. I don't understand the philosophy. I know you guys spent a long time explaining, explaining it, but I don't agree with the approach that you either believe in, you know, there's a market size or you don't, because it doesn't seem to have a lot to do with belief.

It's always bolstered by data. You know, like I remember Camille talked about market size too, and there's data on this stuff. And like, you know, like a market is growing by this much, or this many people will own electric vehicles or the price of oil is going up. So you obviously are way more studied in this.

So you must know things that I don't, why does it come down to emotion and belief? Because I feel like people probably go into pitch meetings with hard facts. So why are you coming at it like that? 

Jason: [00:58:53] It's a really good question. I think it boils down to a couple things. The thing that you and everyone else should know is that, um, especially at the early stage, when we describe any amount of data, if it's how much revenue we're doing or how many users we're doing, or how much revenue we're going to do in a year, or how big the market we're going after is, is like, they're all

kind of finger in the air estimations. And not only that, but it's. If I tell you the very specific number today, that doesn't mean what the future will be either for my company or the market or the market that I'm going after. And so market sizing is important. And in my opinion, it's, it's only important in a sense of like, how does the founder think about it?

And it's like a reflection on the founder's ability to analyze things. But at the end of the day, it's like part of what we were saying, what Christina and I were saying was like, it's kind of still a bet on the founder. It's a bet on the the founder's interest in, in building a gigantic business. That's what you want to find out.

And so it's like you could land in any market. And if the market is not itself massive, if the founder wanted to build a really big business, they wouldn't just stay in that one specific market. They would be like, how do we grow this? How do we make them the addressable market larger let's let's add on a tangential business.

Let's like, let's expand to this space over here. And so not everyone may agree with that, but that, that is certainly my philosophy. And it seems like Christina had a similar one. If 

Olivia: [01:00:38] I'm a founder hearing what you just said, I guess, how do I apply that? Does that mean that I need to show. That my market is adaptable.

Like we're pretty confident this market is huge and this is our plan to like, grow in that. But would it be wise to have kind of contingency plans in, in their pitches and stuff? 

Jason: [01:00:59] I think it, I think it's kind of like, this is like, I don't know exactly how Christina's pitch went, but for her early on when people weren't sure how big SOC2 compliance limits the market for SOC two compliance would be?

I think I would say something like, look. The internet is not getting more secure. The internet, the internet is getting less and less secure, and that is producing huge opportunities to fix the internet for businesses. 

Olivia: [01:01:26] I get it that you're talking about how she shifted to like, okay, well actually at the heart of it, we're internet security, like, and that's how she enlarged the market. 

Jason: [01:01:37] This large vision.

But what we're focusing on right now, which is a huge, acute problem is SOC2 compliance. And you can believe that it's big, or it's not, it's large enough for sure, for me to like, start really solving problems in this space. And so people would bet on both, maybe SOC2 compliance is larger than I thought it was.

And Christina at her, you know, in our hearts, our heart of hearts, wants to solve a big problem around internet security. 

Olivia: [01:02:05] Okay. That's cool. So it, it might be smart to tie your idea to. The biggest possible interpretation of the problem you're solving. 

Jason: [01:02:14] Yeah. Like a bigger general vision.


Olivia: [01:02:17] Okay, cool. That's really smart. Okay. My last question here is like, what the heck were you guys talking about? Okay. This is what I heard. I don't even think this is the actual words you guys spoke. Okay. There was a Medium post about like being a lion, not a dog as in like a dog that barks, or was it a lion?

Not as in like a polka dot, like, I don't even know what words you guys were speaking, but what is that post. Oh, my God, wait, not lines like a straight line. 

Jason: [01:02:50] Line, like a straight line, but lions not dogs is not a bad followup. Blog posts. I'll tag, mark Schuster in this to see if he'll he'll write a lions, not dogs.

First let's spend two seconds. It's a, it's a famous post by mark Schuster. Great blog post about how investors invest in lines, not dots. So if you show up on their radar as one specific dot, it's going to be very hard for an investor to say like, Ooh, I wanted to invest in Olivia. Yeah. But if you've had an opportunity to have an initial touchpoint with an investor and show progress a few months later, and then maybe have some sort of media posts that they see, they are able to then start looking at a line and see a trend line for an entrepreneur and then say, huh, that's a great, you know, Olivia's a great founder.

I'd like to invest in it. So that's investing in a line.

I see a wide range of startups on a regular basis. It can get easy to get tunnel vision around spaces. I find exciting. For instance, I've loved hearing about web three data science, collaboration, and climate tech, because of those blinders. I love asking other founders what spaces they find interesting.

Christina: [01:04:08] Bobby Pinero, who ran finance at Intercom for like eight years is building one of the tools he wished he had so it is actually a, it's a really good, I think a bit of passion, a lot of problem. And he was just like very sharp and it was like whatever he had assigned or Intercom from 20 people or something to like hundreds, you know?

So I'm pretty excited about that one. What else? I mean, I love this is not founder specific, but space specific. Like I love. What's now called the creator economy. Like this is back to like USV and Kickstarter days, but just the, like, how do you support people who are doing something between making art and having a business online?

And there's a very large, you know, big range in between those. But I just love those businesses. And those founders often are like the passion sort, and have these incredible stories.

Jason: [01:05:07] Thanks a bunch for listening. There are tons of insights that each founder we cover on funded has around startups, fundraising, and life, and we don't have time to cover it all. So if you'd like to get a free insights pack based on Christina Cacioppo from Vanta go to If you have any questions about today's show, or maybe you're raising money yourself and want some help problem solving.

Find me on social I'm @jayyeh that's J A Y Y E H. Or shoot me an email at I'd love to hear from you. This episode was produced by Olivia Rheingold. "Hello." Thanks also to Jordan Pascasio from Adamant Ventures." Hey guys." And thanks to Christina for giving us that gem of an investor question.

I'm definitely using that with guests and sponsors for funded in the future. So, what do you like about Funded? As always one last thanks to our fantastic sponsor. DocSend- the most trusted document sharing platform.

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