In short
Podcast Episode Summary: Christina Cacioppo, Founder & CEO of Vanta
Podcast Overview Title: The Social Radars Hosts: Jessica Livingston and Carolynn Levy Episode: Christina Cacioppo, Founder & CEO, Vanta Description: In this episode, Christina Cacioppo shares her journey, emphasizing critical lessons learned as a founder, including self-taught coding, focusing on customer needs instead of investors, and the importance of discipline in building a successful startup.
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Key Themes and Highlights
Introduction to Vanta
- What Vanta Does:
- Vanta is a trust management platform that focuses on automating cybersecurity and compliance processes for companies.
- Simplifies the process of securing customer data and obtaining recognition for compliance efforts.
Christina's Journey
- Early Experiences:
- Background in venture capital at Union Square Ventures (USV) before transitioning to founding Vanta.
- Notable experiences at YC Demo Days and an early fascination with the startup ecosystem.
Founder's Mindset
- Learning to Code:
- Christina taught herself to code to solve the problem of her lack of technical skills, viewing it as essential for starting a software company.
- Emphasized the discipline and commitment required to learn programming independently.
- Customer Focus:
- Prioritized talking to customers over seeking investment initially, showcasing the importance of understanding market needs.
- Waited until reaching $10M in ARR before raising a Series A, exemplifying confidence in product-market fit.
Lessons from Silicon Valley
- Varied Paths to Founding:
- Highlighted the diverse journeys of successful founders and the many different backgrounds they come from.
- Reinforced the idea that there is no single path to entrepreneurship.
Building Vanta
- Initial Steps:
- Transitioned from creating a spreadsheet for SOC 2 compliance to developing a full-fledged product after validating the market need.
- Utilized customer feedback to iterate on the product, ensuring it addressed real needs.
- Sales Strategy:
- Focused on annual contracts to stabilize cash flow and minimize friction in the sales process.
- Worked closely with early customers to refine the offerings and build a strong product foundation.
Reflections on Female Entrepreneurship
- Representation in Tech:
- Acknowledged the importance of increasing the number of female founders in tech.
- Expressed a desire for the tech landscape to become more inclusive, where female-led companies are the norm, not an exception.
Closing Thoughts
- Christina's journey is portrayed as a blend of resilience, adaptability, and a strong focus on genuine customer relationships.
- Acknowledged the support from peers and mentors in navigating the startup ecosystem.
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Key Takeaways
- Discipline & Agency: The importance of self-discipline in learning and executing key tasks as a founder.
- Customer Insights: Prioritize understanding customer pain points over seeking early-stage investments.
- Building Responsibly: Startups should focus on sustainable growth, managing resources wisely while aiming for product-market fit.
- Community Matters: Leverage the startup community for support and resources; peer relationships can significantly influence success.
- Encouragement for Future Founders: Aspiring entrepreneurs should recognize that diverse backgrounds contribute to success and that there are many paths to becoming a founder.
Reflection Prompts for Listeners
- How can you apply Christina’s lessons on coding and customer focus in your own entrepreneurial journey?
- What steps can you take to engage with your potential customers before building your product?
- In what ways can you contribute to increasing diversity within the tech startup ecosystem?
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This summary encapsulates key discussions and insights shared in the podcast episode, showcasing Christina Cacioppo's experiences and philosophy as a founder.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOUnderstanding Vanta's Role
0:45 to 2:50
Discussion on Vanta's function in cybersecurity and compliance.
“Helping companies build out their security programs and then go get credit with their customers for all that work.”
Early Career Connections
2:50 to 5:25
Recollection of past interactions and experiences in the tech industry.
“How did you land a job at Union Square Ventures?”
Navigating Union Square Ventures
5:25 to 6:40
Christina shares her journey and experiences at Union Square Ventures.
“in the batch yeah that sounds right 40 yeah and I think we'd go in and I remember going in when it was sunny and we'd leave when it was dark so whatever that you know I don't know started at 5 6 p.m.”
Insights from Demo Day Experiences
6:40 to 10:00
Memorable moments and lessons learned from YC Demo Days.
“And I remember my thing was like, okay, you know, like we're not going to drink.”
Lessons from a VC Career
10:00 to 12:00
Discussion on the diverse paths to founding a startup and experiences as a VC.
“founder and so many ways to found a company.”
The Journey to Learning Coding
12:00 to 14:00
Christina discusses her motivation and experiences in teaching herself to code.
“I mean, I joke, but like in, again, in two years, they probably gave me like four weeks of work, like actual work to do spread over two years.”
Starting the Journey
14:00 to 14:20
Christina discusses her early doubts about coding and starting a software company.
“And I know you've talked about this before, but I really need to hear it again.”
Overcoming Coding Fears
14:20 to 15:00
She reflects on her apprehension about coding and the encouragement she received from mentors.
“So I think in that, like meeting lots of founders, there's lots of ways to do this.”
Financial Preparations for a Startup
15:00 to 16:40
Christina shares how she saved money to support her transition into tech and coding.
“It was not like totally a finance bonus, but it was somewhere between, you know, finance bonus, like classic finance bonus and no startup.”
Learning to Code
16:40 to 18:20
She details her approach to learning coding and her experience with online courses.
“And but I couldn't also like I also seem confused because I couldn't actually articulate what I was doing beside like I want to learn to build software.”
Show all 35 chapters
Building Her First Project
18:20 to 20:00
Christina discusses her first web app project and the lessons learned during development.
“No, because it's hard and time consuming.”
The Power of Persistence
20:00 to 20:20
Christina emphasizes the importance of persistence in learning to code.
“And so, and that office was basically across the street from USV.”
Navigating Social Circles and Costs
20:20 to 21:40
She reflects on the challenges of social life and living costs while pursuing her coding journey.
“But I do that from, you know, nine to six, nine to seven, right?”
Documenting the Learning Experience
21:40 to 23:20
Christina reads a blog post reflecting on her personal journey and the challenges faced.
“And it's easier to do without a family than with one.”
Advice for Aspiring Entrepreneurs
23:20 to 23:50
Key insights shared for those looking to start their own ventures.
“And at USV, I got to see some of those companies and while they did this and that and they have a billion users, the in-between is not a lot.”
Facing the Reality of Startup Life
23:50 to 25:00
She discusses the difficulties of building a startup and the realities of early failures.
“I think I just didn't want to start a startup that I didn't believe in because I saw people do that all the time.”
Finding a Place in the Tech World
25:00 to 26:40
Christina explores her feelings of inadequacy and desire to join the tech community.
“You can always make it better, but we're at some baseline level there.”
Joining Dropbox and New Opportunities
26:40 to 28:00
She narrates her decision to join Dropbox and the opportunities it presented.
“I'm going to ask you when because I don't remember because you were dating Patrick Collison of Strait.”
Inspiration and Early Coding Journey
28:00 to 29:14
Christina discusses her self-taught coding journey and the influence of her partner.
“So he emailed you because he wanted an in to USV, and I'm glad I had met you, and I said, oh, email Christina.”
Navigating Job Interviews at Dropbox
29:14 to 31:04
Christina shares her experience with unconventional job interviews at Dropbox.
“at Dropbox and you have all these resumes and you have MIT grads and Stanford CS.”
Challenges of Product Development at Dropbox
31:04 to 37:35
Christina recounts the difficulties faced while developing products at Dropbox.
“That is sort of one of the things that inspired you to get into the compliance automation business, right?”
Reflecting on the Transition to Startup Life
37:35 to 40:13
Christina reflects on the transition from Dropbox to starting her own company.
“Here's the 74 pages of information to back it up.”
Finding a Market Need for Vanta
40:13 to 42:00
Christina describes the process of identifying the need for compliance solutions.
“So did you step away thinking, I'm going to tackle this hideous like compliance quagmire?”
Initial Development and Spreadsheet Creation
42:00 to 43:55
Learn about the decision-making process that led to creating a spreadsheet for SOC 2 compliance.
“I want to also note the rule was we weren't allowed to build anything.”
Understanding SOC 2 Requirements
43:55 to 46:09
Discover the key elements and requirements of SOC 2 compliance and how they are structured.
“Anyway, so we made the spreadsheet for segment.”
Researching SOC 2 and Learning
46:09 to 48:45
Explore the methods used to gather knowledge about SOC 2, including talking to experts and analyzing existing SOC 2 reports.
“Google, Salesforce, Zendesk and then actually just like opening all of that.”
Developing a Product for Startups
48:45 to 51:02
Learn about the motivation behind creating a product for startups and the importance of understanding user needs.
“And then they might've built their own software.”
Navigating Y Combinator Experience
51:02 to 54:08
Hear insights into the Y Combinator experience and how it helped shape the startup journey.
“And if you're B2B, it should be revenue.”
Fundraising and Investor Relations
54:08 to 56:05
Understand the strategies and experiences related to fundraising and dealing with investors post-YC.
“And then the advice I got was, but like, let's meet the week after.”
Investor Engagement Strategies
56:05 to 57:14
Learn effective strategies for engaging with investors at the right time.
“Like, I look forward to talking to you at the time we will talk.”
Managing Growth and Burn Rate
57:14 to 59:20
Discover the balance between managing cash flow and hiring effectively.
“And like the answer was kind of always get the customer.”
Pricing Strategy Insights
59:20 to 1:01:22
Understand the process of setting an effective pricing strategy for startups.
“The other thing we did, which was more purposeful, and shout out Peter Reinhardt from Segment, is he had a blog online that had like five posts on it.”
Female Founder Perspectives
1:01:22 to 1:02:55
Explore the challenges and experiences of being a female founder in tech.
“And then when I was kind of after YC, when I was selling a bit more, I would try to do the like, oh, if somebody doesn't blink, when I tell them the price, I'll tell the next person the price two times higher.”
Reflections on Success and Future
1:02:55 to 1:04:07
Reflect on the journey of success and thoughts on future endeavors.
“there on YC's leaderboard for successful startups with a female founder.”
Key Takeaways from Christina's Journey
1:04:07 to 1:07:48
Highlight essential lessons and takeaways from Christina's entrepreneurial journey.
“And so like, I'm going to cry only because I'm so proud and happy about it, but just, just keep doing what you're doing.”
Transcript
Automatic transcript. May contain errors.0:00Carolyn, I am so excited. Today we have Christina Cassiopo of Vanta, the founder and CEO of the Trust Management Platform. Welcome, Christina. Welcome, Christina. Thank you so much for having me. I am so excited to catch up with you today because, first of all, I was recently listening to a podcast and you were talking about what Vanta does. And just for layman, because sometimes, you know, my family in Boston listens to this and they're not technical. When we describe it as a trust management platform, I'm going to dumb it down a little. cybersecurity and compliance automation, dumb down even more securing customer data.
0:46Yes. Right? Yep. Is that correct? Helping companies build out their security programs and then go get credit with their customers for all that work. So maybe through an audit or a questionnaire or like a status page, but like you did all the work, get credit for it with your customers. I was listening to a podcast thinking, oh, gosh, I got to sort of learn about this. I was gripped. In the same way I was gripped with Flexport. Carolyn, do you remember how into learning about like container shipping I was? Logistics is awesome. logistics. I became so fascinated by this industry, this category that you guys created.
1:25So we're going to come to that. But I want to go way back because actually, our paths crossed a long time ago. Did you used to come to Demo Day when you worked at Union Square Ventures? I did. I got one of the perks that I got to go to Demo Day and I remember meeting you there. Yeah. What year was that? Like bring us back to back then. Okay, summer 10. And it's like end of August. And you had already graduated. Like you were how old? I was summer 10. I was 24. Okay. I had done, unlike most of Silicon Valley, I did extra school. So I did like five years of a bachelor's master. So I was like basically one year out of school.
2:05At Stanford. Yep. And you were from the Midwest. From Ohio. So it must have been just mind blowing to arrive in Silicon Valley back then. Yes. I mean, stuff was happening. Stuff was happening. It's funny. I was totally the girl from the Midwest where I remember even Ad Met Weekend and just being like, the sky is so blue. You know, and like 60 % of Stanford students are from California, right? So just like, what are you talking about? But it was, I don't know, the sky is more blue in Northern California than it is in Ohio, like kind of ever. Or are we just optimists when we live there? Also that, probably.
2:44Well, also, there's no hills in the Midwest. Right. Right. So it's like it's also super flat. Yes. It's not flat in Northern California. No palm trees. Yeah, no palm trees. How did you land a job at Union Square Ventures? Dumb luck, truly. You know, one of the many things I respect about the USV guys is they've always hired off the internet. And so I started reading Fred's blog. And at some point in the summer of spring, March or so, he'd written this post and said, hey, we've had this analyst for four years and he's great, but he's moving to Boston. So we need another one. If you're interested, send us some links to your web presence.
3:25And I read that and was like, what even is this? This is 2010, right? You're like, what? Like this both sounds great. And like, who is going to get this job? Like what crazy person? And sort of had that mindset about it, but kept thinking about it. And then, of course, literally 30 minutes before the, like, form was supposed to close, I sent four links to my web presence. No other words, nothing else. And they hired me. What was your web presence back then? Yeah, I was just going to say, what was it? It was 2010. Flickr. Twitter. I had just my, like, year after school I'd spent in Berlin working at a design lab.
4:07and I'd like kept I started a blog because I wanted to be like a design blogger and so I had this like streets of Berlin not very good to be clear blog um and it was maybe a tumblr but it was basically that okay I wonder if you had uh more web presence than the average you know like because I'm just thinking like that's a lot of kind of cool stuff yeah I think there was some of that I think also you know in retrospect I like knew people at Stanford who knew them was not like didn't didn't that didn't even occur to me to use any of that which was kind of kind of silly and very naive and retrospect I think but just kind of makes me like respect those guys even more because like they truly did hire off the internet and like yes it ended up being a Stanford person but it wasn't uh you know was not a Stanford connection so I want I want to ask you first of all what you remember from the early demo days that you came from I'm just curious and also I want to talk about your time at Union Square Ventures because I feel like you learned some some good lessons there yeah okay so early demo days so these were in Mountain View like that building Pioneer Way that was our office yes I think yeah yeah and I think actually I have I still have my like list of kind of want to pull it up but like there were probably 40 companies max in the batch yeah that sounds right 40 yeah and I think we'd go in and I remember going in when it was sunny and we'd leave when it was dark so whatever that you know I don't know started at 5 6 p.m.
5:37I think when I started the pitches were like three and a half minutes or so maybe four yeah comparatively so I'd sit there with my like notebook and your printout my pen and I'd like write notes on each company and I'd sit there you know and like try to figure out which were in USB parlance, large networks of engaged users. Right. And then you do this. And I also remember Paul in the beginning doing getting up and being like, okay, like, you know, you're at YC demo day, like, there is an Airbnb in this batch. I don't know what the Airbnb is. This is your job to figure out you are smart investors.
6:16But like, you will find the Airbnb in this batch. Like, now we will start. You know? Exactly what he said. Yeah. It is. It was like kind of like a circus ringleader, but in this incredible way. Like it was just like, and now the show will start. It's all demos and like scrimpling notes. And then there was like a cocktail hour. You didn't call it that, but there was like a cocktail hour. Yes. Afterward. Like beer and buckets and some wine. Yes. Yeah. And I remember my thing was like, okay, you know, like we're not going to drink. Cause like I'm at work. But you're going to go around. And I always kind of tried to be basically the last one in the room, like the last investor.
6:57And so I remember, like, I don't quite need it, but I think I was like in the, you know, single digit count of investors left. Right. And just trying to, like, talk to folks who are like not like not interested in me, but like really interested in USV. And you're like, yeah, I understand. Like, let's talk about USV. We do that. And then it would be really dark. And on 1030, 11 p.m. and I'd like get in my little rental car again, 2010. and like rental car myself back to the Hilton or whatever it was. And then wake up the next morning and like type up all my notes to this email of like, here's all the companies.
7:30And like, and then here's like the three or five that I think were interesting. And then inevitably I'd get an email back and be like, no, those aren't like this other one is, you know, and you're like, okay, cool. I'll like try to go set that up. But it was very fun. Do you remember any big win? Yeah. Did you pick a winner? Sure, did you find the Airbnb? Because we all know Fred Wilson passed on Airbnb. Yes. That he famously acknowledged. Well, I was going to say, when I walked into USB in 2010, the cereal box was on the shelf. Like that post in that story, it was not – it's true. That cereal box sat on the shelf.
8:06So it was very true. No, I definitely didn't. There were a couple companies I really liked and I didn't get them to invest in and actually got to know the founders. And now they're friends. But, like, they were not in the top whatever exits of YC. So, you know, USVU was more right than I was deeply. You must have like learned so much working at that firm and meeting with so many founders. Like, what do you remember as like high points from your time as a VC? Yeah. Actually, before I answer that, can I give you one more YC demo day? Yes. Yes. So, okay. So I'd go, you know, winter and summer and show up and kind of rerun that playbook.
8:42And I think it was summer 12. I was, I think it was a two day demo day or like a two, a split. Yeah, it was a big batch. Yeah. And the day I was there was the day Steve Jobs resigned from Apple for help. And that happened, like, in the middle of someone's pitch. And I still remember sitting there and there's enough people with iPhones and people just are whispering. And, like, the poor founders were, you know, were, like – and then basically, like, they finish. And I think somebody is, like, we need a moment. You know, like, Steve Jobs just left Apple. And I remember getting that news sitting in like the demo day folding chairs.
9:22You were in the computer history museum at that point. Yes. I don't remember that at all. I don't remember either, Carolyn. I'm pretty sure. I'm so glad you told that story because what a moment. Yeah. Huh. And it was kind of, yeah, I think we knew enough to be like, oh, this isn't good. Like this is serious and not good. And who knows what happens next. Like he's not coming back. Yeah. But like this is not a man who would do, you know, who wants a vacation. Yeah. would do this if he had a choice not to. What an interesting memory. So tell us about your some of your important takeaways from Union Square Ventures.
9:57Yeah, so I think building off some of this, I think one of the primary ones that's sort of underrated is there are so many ways to be a founder and so many ways to found a company. And which sounds like vanilla and milk toast when you say it, but like, I think I like deeply didn't, you know, like in my head, it's like, oh, no, you've got to like start programming in your four, go to college, study CS for like a semester or two, drop out, maybe wander in the wilderness, maybe just like make something then a billion people use, but like, right. And then you just go do that. And like people do that.
10:32And that is wonderful. And then like some people do that. And some people are college professors and some people are lawyers and like everyone finds their path, you know, and like that, like a slightly more sophisticated model, but that was like basically my model of the world. And I think, you know, among the many things, one of the things I'm really appreciative of USC for is I worked there for two years and I probably met five founders a week on average for, you know, 104 weeks straight. And so you just meet so many people and see so many ways of doing it. And that was really helpful, uh i think for me because it kind of broke that like oh i don't have that you know i don't have that history and so ergo i should like should i be a lawyer not quite but like should i be a university professor and i was like no there again there's there's lots of ways to do it you should do it for a way that works for you i think that's a great observation because i feel like i noticed that at y combinator like there's so many different paths to becoming a founder and different types of people and different ways they behave.
11:33So it's good to reinforce that because it means you could someday be one. Right. Yes. Quick question. Oh, gosh, what was it? Hold on. It was at the tip of my tongue. It was a random question about being a VC. What do you do as a young person as a VC? Because, like, no one wants to talk to you. Right, because you're not the check writer. Exactly. Yeah. And they shouldn't. Was that hard? did you have to do a lot of sort of cold calls to startup founders? No. So USC wasn't that. I mean, I joke, but like in, again, in two years, they probably gave me like four weeks of work, like actual work to do spread over two years.
12:11So it was a lot of like figure it out. And I think in the beginning to that, and like, you know, PG's essays of like, don't talk to the young kid at the VC firm, which I think is actually generally correct. I think when I was in that role, I was like, oh, that is right. Why would someone talk to me? What is it I'm supposed to be doing here? what would I say my job is? And I think it took me six plus months probably. But what I figured out was like, yes, no one wants to talk to me. They want to talk to Fred, to Brad, to Albert. Some people unfortunately get stuck with me. Sad for them. But like my job is then not to pretend I'm Fred because that will annoy everyone.
12:46I am not. Right. My job is to be like, let me try to understand you founder your company translate that into usv language route you everyone wants to be with fred because it's fred and he's wonderful but like if it's a dev tools company they should actually talk to albert do that then go to albert and be like albert i met jessica she's working on blah blah blah when you hear it you're gonna think a it's actually b like and then this is gonna happen but like this is this is why i think it's interesting can i set you up and kind of do the same to the founder. I'd be like, founder, you're going to explain this.
13:21They might get caught here. So just know that and like da-da-da-da-da. And then like make that meeting work. An important conduit. Yeah. And like that, I think that was when I felt like I kind of, I don't know, hit a stride. It's a big word. It was a big phrase, but like, it's like, oh, okay. I think this is useful. Or given this role exists, I think this is a like reasonable way to play it. And I think that would be really interesting if I were 22 or whatever, you know, in my early 20s. Now I want to ask you about probably what I'm most fascinated with about you, because it's something that we advise all the time and no one actually does it, which is you taught yourself to code.
14:09And I know you've talked about this before, but I really need to hear it again. And tell us about how you decided to do this, what you did, that kind of thing. Yeah. So I think in that, like meeting lots of founders, there's lots of ways to do this. I can do this too. I had one, well, I probably had several, but I had like at least one really big hang up. And it was that I couldn't code and I wanted to start a software company and couldn't make software. And logically knew, I mean, again, having met with lots of people, like lots of people who can't make software start software companies and can be exceedingly successful.
14:46And I just felt like that's not me for good and bad. But a deep truth about me, I think, was I don't feel like I am able to do this unless I can make software or able to try to do this unless I can make software. And also, as I was leaving USV, Fred said something to me, which is like Fred is, he doesn't always come off this way I think but he was exceedingly perceptive and I remember talking to him and him being like oh you're not a fake it till you make it person so like don't try to do that Christina and sort of being like oh is that bad you know like deer in headlights but I think it's also like just very true and something that's worth given that worth embracing anyway and so what I did was I had saved my bonus which USV at the time had had bonuses, which like, you know, tech jobs generally didn't.
15:43It was not like totally a finance bonus, but it was somewhere between, you know, finance bonus, like classic finance bonus and no startup. Which, by the way, is another bit of advice I always give to young people. Like, if you want to start a startup, what's my first bit of advice? Learn to code and save your money. Yep. And so what I did was I quit USV and I lived off my bonus for a year and a half. and everyone else thought I was crazy. It's like I, and I think maybe it was a little quarter life crisis-ish, but you know, with some quarter life. Right, exactly. You know, as those seem very important when you're, you know, 25.
16:20Right, right. And I was like, no, I want to do that. And people are like, are you starting a startup? And I'd be like, no, I'm coding. And they'd be like, so you're going to go to a master's program? And I'd be like, no. And they're like, you should really, you seem confused. You should get an MBA, right? And then I was kind of like, but then I have to pay$200 ,000 on top of living expenses to like do what I'm doing and also like have more random flights to Ibiza or something, you know, like not my jam. And but I couldn't also like I also seem confused because I couldn't actually articulate what I was doing beside like I want to learn to build software.
16:56People are like, for what end? And you're like, unclear. Like, hold my beer. I'll get back to you. It's like sort of my answer. So how are you teaching? Were you taking like online courses or what? Is that what you did? So this was the year. This was like the era of like all the coding boot camps. But I was sort of like, do I really? Like I don't want to try to do this myself. So where I started was Steve Huffman's Udacity course. What? I love all of this. Why is he overlap? Especially with Huffman. Oh, my God. His Udacity. His Udacity course, which was how to make a blog in Python. so I watch it and you basically just like type what he tells you he makes a blog in Python um and then I was like okay well you know I don't really have a startup idea um but I was and I'm still really into books and reading and bookshelves and if I like go into someone's apartment I just kind of want to look at their bookshelf you like learn so much about them from their bookshelf and then there's like lots of jumping on conversation points whatever so it's like okay I'm gonna make a bookshelf website it's also why people thought I was having a quarter-life crisis because like you know I'm not they'd be like are you competing with Amazon um it's like no no no I'm making a bookshelf website uh again and they'd be like what are you doing with your life but anyway so I like took my blog where you'd like post to a blog and you're like oh you post a book to the blog okay you post a book to a shelf and then I made this web app that was you know lovely in some ways and like deeply terrible in the ways your first projects are always deeply horrible 5 ,000 line main.py file like you know you you kind of mess everything up but you learn along the way and so that was like the very first thing and I built it and it worked and I had like lovely and wonderful friends that would like go and like shelve five books when I asked them and you know they'd hit some error and I'd be like oh I don't you know whatever I have to go figure you know right like it was that but like then I got to see their books um and it was like the first like oh my god I made that well you know and it took i don't know three four months because i didn't know what i was doing and you didn't i didn't know how to deep like not only like i just didn't even know how to debug like the meta of debugging all of that but like i don't know you slug through it mostly yeah i just like it's just so amazing because so few people actually do that they think yeah i'd love to learn how to program but they won't slug through it including myself i have said for so many years I should learn to program.
19:18And have I done it? No, because it's hard and time consuming. But you did it. And I think I heard you describe it is you treated it, the process as a job, right? Kind of to the like, should I go to school for this? It was like, no, but I need to, you know, like, not get up and be like, I'm tired today. I'm going to get up two hours late and maybe I'll put on shoes. You know, you're like, can't, can't get to that. Like, am I perpetually on vacation land? and so um new york tech was small chris dixon had just sold his company hunched to ebay oh yeah and they had moved to new ebay new york which was this like nine quadrillion not a real number but like nine quadrillion square foot space that was empty and he was kind of in the mold of like so it's right before he went to andreason and a little yolo i think and so it was like whoever wanted to come hang out in the hunch office he would just give you a desk because he had acres of desks.
20:10And so, and that office was basically across the street from USV. And so my thing was like, look, I'm just going to get up and I get dressed. And I like walk to the same place I've walked for two, you know, like I just like basically do the same thing I've done for two years. I just sit across the street and type. But I do that from, you know, nine to six, nine to seven, right? Like it is a job and I show up every day in a place where people show up every day and type things. Did you ever think about leaving New York just to save money? Because I'm sure your whole social circle was there, but like, you know, it's an expensive place to live.
20:42Yes. I think I was too – like, losing the social circle was hard because you're like, I just blew up everything else in my life. Like, should I totally do it or like, hang on to the shreds I have? But it is funny because it was, you know, I call it like, it was grad school and that, you know, you're like, don't really go out to eat, did not get in a taxi for a while, you know, like all of that. Subway for you. Yeah, exactly. I have to read something. I try not to do this, but I found something that you wrote, you blogged about this on your website as you were in the middle of this. And Carolyn, I have to read it to you because I swear, Christina, this could apply to someone today.
21:23And I feel like it might inspire some people. I'm going to read a couple of bullet points. If you've left your job to make things, figure out a way to explain that to your parents. when you don't have a job most people will assume you're not working don't be mean to those people they're confused not malicious like most decisions this one wasn't as risky as it seemed if you're the sort of person who can afford to quit his or her job to make things everything will be okay regardless of how this all turns out and then lastly i'll just read this one that said this This is one of those things that's easier to do in college than after.
22:02And it's easier to do without a family than with one. But whatever your situation, thousands of other people have done this. Given time and effort, you can too. I just love that. Oh, I want more people. Yes, it's such good advice. I mean, I feel like anyone thinking of doing a startup, learning how to coach, you just paste that to their mirror in the morning. it's funny to hear that because i can both hear the i am definitely giving myself advice and a pep talk in writing that and the like kind of ire of being like stop thinking i'm not working because i don't have a job i am working hard you know and like i can i can kind of hear all of that and and yeah you read it maybe we'll train other people not to assume you're not working just because you're learning how to code.
22:54Because I think that that's the most, I'm like envious that you did that. Basically this whole questioning is like, I wish I had done that in my 20s when I had the time. Okay, so now you're learning to code. Tell us what happens next in your startup journey. I make a bunch of stuff that no one uses. Lots of stuff. I have a list of it on my website now on purpose. because I think another thing, backtracking a little bit, but another thing I learned at USV is sometimes on purpose and sometimes not, a lot of these startup stories are told as these linear, I did this and I did this and then I had a billion users and then I was a success.
23:37And at USV, I got to see some of those companies and while they did this and that and they have a billion users, the in-between is not a lot. like the end between is like a crazy topiary maze and in the vein of like kind of lots there's lots of ways to do it and humans do this not just like um i don't know gods like i feel pretty strongly about uh talking through the messy middle of things anyway so my messy middle is yeah made a bunch of stuff no one wanted was quite sad about that uh because as much as i told people oh i'm just learning to code and i don't want to start a startup i definitely wanted to start a startup.
24:16I think I just didn't want to start a startup that I didn't believe in because I saw people do that all the time. And I saw how it is awesome at first because you're NYC and then you raise money and then you have to work on the thing, you know, like then it is terrible. So I had probably somewhere between a healthy and an unhealthy skepticism of that. I got to a point where it was probably two years. I did not have a ton of money in my bank account And was kind of like, man, I am tired of bodega sandwiches and bike rides. I feel like I'm very old now. In retrospect, I'm probably not that old, but I felt very old.
24:51I felt like I'd gotten to a place where you're like, oh, I can build something. Is it the best thing in the world? No. But I can get the thing in my head onto a screen for feedback that then I can make it better. So kind of box check there. You can always make it better, but we're at some baseline level there. But what am I actually doing? My friends, my peers, whether they were founders or working at companies, they were like advancing. Right. And here I was and I'd kind of never worked at a company. Again, I'd worked at USV, but it's a five person venture firm and you all know how USV works.
25:24And it's like wonderful and lovely and like not a company. Right. And I only sort of had co-workers. And so it was just this also part where it's like, oh, my gosh, how unsocialized am I? Like, how do I like what is a company like what? it feels like everyone is so far ahead of me and I think I can catch up. But like, I'm also not even in the stadium. Like I'm five zip codes away right now. Wow. And so there's like a bunch of feelings and emotions and sadness around that. But I think it was also like, well, what am I going to do about it? You know, like, am I going to keep staying five zip codes away?
25:56Am I going to try to get in the stadium? And so I ended up joining Dropbox as a PM because I basically had a bunch of friends who worked there, including a startup I had tried to get USV to invest in and they didn't, called Hackpad. Oh, yes. I remember that. Yes. And so I joined the Hackpad team to work with the Hackpads. What were their names again? Igor and Alex. Igor and Alex, the Hackpad founders. I definitely remember them. Okay, so you worked on their team at Dropbox. Another, you know, YC connection point here. Also, I need to throw in here, I met you on a more personal level around this time.
26:43I'm going to ask you when because I don't remember because you were dating Patrick Collison of Strait. Yeah, it's actually reverse. You introduced us. Is that true? It's true. What are you talking about? I'm about to fall out of my chair. Almost. Okay. Tell me the story of how we introduced you. I'm all ears. So summer 2010 demo day. Oh. I think you come, you come find me and say hello. And it was like, oh, USC told me they hired you like, hello. Like, I was like, oh, this woman is so nice. What's y 'all? You know, and then like somebody pulls you away and you're like, here's Harj. Harj is also great.
27:22And introduced me to Harj. because he was a partner that he was a good partner then first end and we talk and go on my ways whatever and then like three weeks later I get this email being like hi Christina like my name's Patrick I want to pitch Fred but he's out of town so I figured I'd email you and also Harge and Jessica told me you were nice so like want to get coffee oh my gosh keep going he was for business, not for personal. Correct. At that point. Okay. Because I would have remembered if I had officially set you up. No, no, no. But it was the, yeah, everything goes back to the summer 2010 day.
28:03It really does. Oh, my gosh. Oh, my gosh. So he emailed you because he wanted an in to USV, and I'm glad I had met you, and I said, oh, email Christina. Yes. And then, you know, you started dating? You guys hit it off? A year, two years later. Okay, a couple years later. Oh, so there was a lag. So did he inspire you? Because he had at that point started Stripe. Like, did he inspire you to, you know, learn to code and that you could do it and maybe start your own startup kind of thing by what he was doing? Yes. And I think just one of his superpowers in life is believing in people more than they believe in themselves in the moment.
28:49and I think I was a beneficiary of that but I think if we like listed out the people who are beneficiaries of that like the list is literally in the hundreds and we all need friends like that it's so great when you meet someone who's like that oh Patrick yeah well can I can I ask like going back for a minute you so you're totally self-taught right when it comes okay you must have gotten really good though because like if you're you're a recruiter you're hiring person at Dropbox and you have all these resumes and you have MIT grads and Stanford CS. And it's like, how do you as a self-taught coder get a job like that?
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29:28Like I'm really impressed. I didn't. So two things. One is a product manager. Okay. Okay. Yeah. To their point, the recruiters did not know what to do with me because I did not look like things they had seen. And so it was funny. So I went through two or three days of interviews because I was kind of doing two or three roles worth of interviews. Yeah. And then you're like, why did they even care this much? Like, with much respect, the recruiters didn't. But I just kind of knew enough people in good standing internally who were just like, no, figure out what to do with her. I see. And I was kind of like, please figure out what to do with me.
30:07And if you need me to run through five obstacle courses, I am here for that. Right. And so then, like, went through all of these. it was like a there was a bit of an engineer there's like this prototyper role they had there was a pm there might have been designer you know like it was just like go through it all and then see what's left at the end but really it was i mean i did well enough i suppose but really it was the people on the inside pushing for me honestly because they knew you were talented and they're like you should let her just hire her she'll figure it out yeah basically yeah okay okay yeah but still you must have done a good job teaching yourself to code because like she did she's being humble okay I was gonna say okay now we're getting I'm sorry for all of this background stuff but it's very critical to like my social radars you know I gotta get to know you deeply before we get in to Vanta because drop when you are a Dropbox paper that that is When Hackpad, sorry, Hackpad, oh my gosh.
31:07That is sort of one of the things that inspired you to get into the compliance automation business, right? Because Carolyn said, do you know why she chose this industry? And I was like, I do, and we're going to find out all about it. So tell us what happened at Dropbox. Yeah. So I think the little broad arcs at the stage was like 2014, 2015 Dropbox, still like height of Silicon Valley power and prowess. But I think it was also a constellation of apps era. And it was everyone being like, oh, but we're not going to have files forever. Dropbox's business is booming and continuing to whatever double, triple, like quintuple year over year.
31:51But it also felt like, I don't know, it felt like that would stop to the day 10 years later it hasn't stopped. but like right it was like they were trying to make a photo app there was like and I think the the strategy was well what do people put in Dropboxes they put in photos so we'll make carousel they might put in email so we'll buy mailbox they have lots of documents so let's buy Hackpad and turn it into a document editor and so that was kind of the overarching piece and then the um what was the paper team or the became the paper team the Hackpad team was kind of blended it was half Hackpad, half Dropbox people.
32:25And it was all the old Hackpad code base. But anyway, and so we, you know, we had them, we were totally separate from the rest of Dropbox. And we thought we were super cool because you're like, oh, we're not doing the old thing that's slow and has a bunch of people and bad process. And like, we are the cool pirates building the new thing. And we were building the new thing. And it was at this, when I walked in, it was this funny level where everyone at Dropbox had moved off of Google Docs and used paper, called it something else but paper at the time and we could not like pay someone outside of dropbox to use the product and our joke was we had two users we had aj's mom aj was an engineer on the team but we had aj's mom who had never seen google docs so thought like real-time editing was magic and we had engineering manager steve's girlfriend and they were our best users and then engineering manager steve broke up with his girlfriend.
33:17Like, actually, I thought we just had AJ's mom. Oh, no! And we kind of had other users, but we, like, sort of didn't. And that was kind of, like, the state of things. Where we would, like, write Mother's Day cards to AJ's mom. You gotta get more than that. And then everyone at Dropbox was like, this is great. Why hasn't it taken over the world? And we'd be like, can we introduce you to AJ's mom? She loves it. Loves it. And so over time, we started to figure out, you know, how can we make something that – or joke – or not joke. Well, we called them. We're Brandon Street Startups. That was our target market.
33:57We're like, we want all the Brandon Street Startups, Brandon Street in San Francisco, like 2016, to like use paper. and we did i think the short version of it is that actually it's made me like the startup within a startup concept is is very tough because there were lots of things we would have done if we were totally independent that we like structurally or legally or whatever could not do because we are part of dropbox and i think in retrospect we were not very we were like too pleased being pirates on an island and we're not good at attaching to Dropbox and taking advantage. So we just kind of had the downsides and not the upsides.
34:41Anyway, and one of those downsides is we were going to launch and we were going to launch a go to Dropbox.com slash paper and you sign up and you get into the product. And we were like very excited because we needed more users than AJ's mom. So we're going to do this and da, da, da, da. And, you know, a couple of days before one of the lawyers walks over to our desks and is like hey you can't launch to dropbox customers right and you're like pardon he's like no you can't you will violate the contracts and you're like what and he's like you know they go they're the contracts and they say things like dropbox is secure and compliant and pen tested and sock 2 and pci and like blah blah and you're like could you spell those words for me like kind of idiot pm was just like what are you talking about anyway carolyn's giving a real like sort of knowing nod here as you're telling this story being the lawyer um so you were clueless you were just like uh really okay yeah and then you're and then you and then kind of then you like try to be less clueless more clueful i suppose and you know like you're like what are these things you're asking me to do and you're like okay like suck too okay like you need an auditor to come in and vet everything so everybody else then thinks you're fine you're like that makes sense cool buy it it's like great wait, in order to prepare for that auditor, you need to take your whole engineering team away from building for a year and take screenshots out of AWS to show the accountant.
36:06And then you're like, wait, sorry, run that by me again. Like I lost you. And it was learning what it actually was and being like, I get the high level. The way you get there seems generously stuck in 1994. And again, Dropbox 2016, height of its power. Like this is how like the, you know, one of the preeminent tech, private tech companies of the day does this. Are you kidding me? Can you quickly just in a sentence or two, just describe what SOC 2 is? Because it's a, you know, big, big thing for your business. It's an audit that software companies go through. And it's an audit against their IT and security practices and policies.
36:48And so the way it works is first the company defines kind of what they're supposed to be doing. and then an auditor who's actually an accountant for weird historical reasons comes in and is like hey you told me you have two factor on everybody's email will prove it to me and you say okay i'll like log into the g suite admin console and show you this page that has all these locks on it and they say great take a screenshot of that with the date and like send it to me and then you do that basically a thousand times. The accountant will then leave. They will write up everything they saw in this 80-page report.
37:25You get this magic PDF. And for the next 364 days, you can send it to your customers and say, hey, you can have confidence in my practices because I just went through this audit. Here's the 74 pages of information to back it up. This is so painful. oh gosh i can't believe this so all these things to make sure that you're checking the boxes and i will say dropbox was very legit at that point but there's a lot of up-and-coming startups that this is the last thing they have time to do or care about so i imagine no one was doing these audits or freezing their development team for a year oh my god i mean it would have cost a lot I mean, Dropbox could have paid for it for you guys to do it in-house, but like your average startup would, I'm assuming, not be able to.
38:16I mean, not just the year of downtime, but like all of it. It was both. Yeah, yeah. It was like, do you want to give your engineering team away for a year? And you're like, no. No, I don't. No way. And so actually when I was there, to that point, Paper did not have a SOC 2. We were like, we can't give away the team. We only have AJ's mom as a user. Like, we got to solve that problem first. They did it later. But to that, it was just like even it was the same thing. Again, even with the resources that Dropbox had, it just seemed like, well, we don't have product market fit. Why would we do this?
38:46Right, right, right. So did you, just out of curiosity to close this story out, did you try to market to non-Dropbox customers? What was the solution? Yeah. Well, yeah. Basically, we used the Dropbox marketing channels to drive traffic, which was mostly Dropbox users slash early adapters, if you're a Dropbox customer in 2016 to a page where they'd log in and then hit a brick wall. And there's many reasons I think paper didn't tick off, but I think this was not helpful in the effort. Okay, so then you decided to start a startup? I think it was a combo of, to all of my jokes, it was like the pirate on the island thing is very cool, but not what this product needs.
39:30The product needs someone and a product leader who will integrate it with the rest of Dropbox. Like, given these constraints, that is the right thing. Like, that's not me. You know, like, and I can try to be that person, but like, it's not me. And so in that sense, it felt like a reasonable transition time. And then I think the background piece is I wanted to start a startup. You know, I kind of felt like I halfway tried, halfway hadn't a couple years ago. I was sort of, again, resentful. I was like, I want to actually try next time. Like if we kind of stepped up to the plate and walked back, you're like at least swing the bat.
40:08And it felt, yeah, it felt like a reasonable time to like step away from paper. Okay. So did you step away thinking, I'm going to tackle this hideous like compliance quagmire? No, not that smart. No, not that smart. Okay. So what, how did you decide to do it? Yeah, spent kind of, you know, did the thing you're not supposed to do. Spent like three months building a bunch of stuff that no one wanted. You know, being like, oh, what if this existed? cool evade it and showing it to people and they'd be like well I don't want it but maybe my friend which you know it's just like a nice maybe AJ's mom wants it exactly it was like we were like back to AJ's mom you know like bad and did that for a couple months you know it's cool because you're building stuff and then you're like wait this is terrible no one wants my things and so the rule was we were not allowed to build anything else we just can talk to people and you can kind of talk Talk to them about whatever you want, but talk to people until you find someone with a real problem.
41:06And one of the things I went to go talk to people about was security, interested in it. And through that, this like SOC 2 compliance concept came up again. And there was this like, oh, wait, I remember that. That was madness. Like, let me go back and look at it. And long story short, Vanta popped out of that. Just to go back really quick, you quit Dropbox and you had to go tell your mom and dad. Again. Guess what? I'm doing this thing again where I just am quitting with no safety net. I'm just going to do this experimental thing again. And they must have been like, wow, Christina. They were. I think it was easier the second time because they'd also – and I also had seen the like, your worst case is you get a job at Dropbox.
41:48That's quite good. Right? You can be angsty about it, but like, man, is that – are you doing fine? Yeah. Yeah, yeah, yeah. So it was like, okay, do it again. Are you keeping in touch with the people at Dropbox? Just in case. I want to also note the rule was we weren't allowed to build anything. We had to talk to people. You slipped that in, but that's an interesting sort of rule that you gave yourself because you're like, it's not worth even building something if the need isn't there. so what was then when you finally allowed yourself to build what was it it was a spreadsheet so to that because like again we could both code but we i think it was like it's actually a lot easier to change a spreadsheet than change code and so it was a spreadsheet what was called a gap assessment at the time they don't really exist anymore but it was like hey company here's what you need to do for a SOC 2, here's what you do, here's the gap, and instructions to fix in great detail.
42:51And so it was this color-coded, I don't know, 15 by 150 spreadsheet that we made, just go back to YC, we made a segment. Oh, another YC, another front and segment, two more YC touch points. Were you friends with the founders? Yeah, yes. And so that was, they kind of let us, It was like, I know you don't know anything about SOC 2, but I know you'll try hard. And also, I need to know something about SOC 2, and I don't want to deal with this. So like, sure, basically, was the trade. So they were guinea pigs. Yes. Okay. For like a spreadsheet. And so we made this spreadsheet for segment, which they liked.
43:33None of us really knew what we were doing, but we did net confines. And then we wanted to make sure we could actually standardize these because the old part of why people didn't think you could start a Vanta movie with Vanta is because every company was unique and special and had different things they do, which is both true. And when you're a small startup, best practices get you like really far. And that was our thesis. Anyway, so we made the spreadsheet for segment. And we then turned around and basically like find and replaced segment for Front and gave it to Laurent at Front. And then we're like, do you like it?
44:09Can you tell it's not for you? And he liked it. And then we had someone else who heard about it and said, hey, can I get a spreadsheet? And that's where we're like, no, you will get a web app. We will start to build said spreadsheet. Wow, that's pretty cool. Tell us just very briefly what kind of things were on this spreadsheet. You have the 2FA. What else? Just so we understand what kind of doors you need to lock around the company. So there's a bunch of, did you set up your cloud infrastructure at AWS well? Is data encrypted at rest? Is it encrypted in transit? Are the, you know, ways you can log into certain machines kind of locked down and known?
44:51Are the permissions all like closed the way you want them to be closed? So it's like a bunch of like, did you set up your infrastructure correctly? Things. Okay. There's then a set of stuff around people, which basically boils down to like, do you have a hiring process? And do people understand what their role is and their responsibilities in their role are? And do you like check in to make sure they're doing them? And so sometimes this comes out as like SOC 2 requires performance reviews, which isn't quite true. You just have to show, like, we have some structure that is baseline reasonable in how we go about doing things.
45:27I'm curious, how did you learn all this? Were you able to learn all this by just Googling and, like, or did you have to interview people or did you have to talk to government regulators? Like, how did you learn? Yeah, a couple things. So one was, like, talking to anyone who would talk to me, basically. Right? And it started with the Dropbox security team and then kind of fanned out. but it was this whole host of folks there. It was, there was some content marketing online but not nearly what there is today. Actually, the other thing that was really helpful was now lots of companies but big companies at the time you could get their Sock 2s and so it was getting Sock 2s from AWS, Slack, Google, Salesforce, Zendesk and then actually just like opening all of that.
46:17opening all of them and just comparing and saying, okay, for this regulation, what do these six companies do? Okay, for this one, what do these six companies do? And I think that was helpful because you read them and you're like, it's all different words, but it's kind of all the same stuff. And again, there's some nuance, but you can 80-20 it. And like kind of realizing, oh, you can 80-20 this, great. That software can solve. So, Levy, are you super excited about this? that you're this is more interesting once it's broken down it's actually really interesting um as a general concept it sounds kind of unsexy and boring but actually the more you get into it the more you realize like oh this i get it like i can see why this is important and it's actually pretty interesting this is what i like was so gripped learning all about all this stuff and i also have a thing I love when startups solve a problem that any startup could then use and doesn't have to build in-house.
47:17Were you thinking about that? Were you like, let's build something that we can just sell to startups, they all need it, and they'll pay us because they don't want to have to recreate the wheel? Yes, and I think in two ways. One was like, I think one thing I have found helpful in product development, and this might be a YC thing, or it's definitely adjacent to YC stuff is if you like your users, you will spend more time with them and you will build better stuff. And so if you like choose users you want to hang out with and whether that's hanging out in person or hanging out in a WhatsApp group, just like you will build a better thing if you like your users.
47:55Yin Wu of Pulley said this. Yeah. She said just practically the same thing. She's like, I got to talk to startup founders all day and it was so much fun. Right. And so I think there was that, you know, and then you're like, especially then you're like, do we want to hang out with startup founders? Do we want to hang out with, you know, GRC professionals at Fortune 500 companies, which is like now more of my day, right? But at the time, you're like startup founders all day long. So there was that piece of it for sure. I think the other pieces, there's an economist named Ronald Coase who had a theory of the firm.
48:26And it was kind of, it was like trying to reason about what does a firm do and what did they like outsource? And there's like all this economic, like microeconomic literature on it, whatever. I kind of like think it's interesting and cool, but to your point, there's like also a practical application here of in the past teams did all of this in house. And then they might've built their own software. Like this Dropbox would like, because it was pre good recruiting systems, like all the recruiting software Dropbox built itself. Right. And then as like a, um, Greenhouse or an Ashby or a Lever got started, right?
49:00Like no one had to do that anymore. Right, right, right. And so I think, what was this, 2016, 2017, like there'd been enough of you'd seen that greenhouse Ashby lever thing enough to be like, oh, this could have that property. And that is a good property to have. Right, right. You can tell Christine is an econ major, by the way, and reads a lot of books. Yeah. You went through YC in winter 18. So what made you decide, hey, we're going to apply to YC? yeah we talked to so clearly knew yc like a new know it very well um what we actually did was talk to a bunch of people who went through it twice really yeah and to be like why'd you do it the second time tell me more and then people who didn't do it the second time you know and i think the like didn't do it the second time those were more similar it was like i know everybody like everyone's an email away like um good sure i think people who did it the second time were like oh no because the cohorting is really helpful the community is real and if you are doing a business and there was a bit like if you're doing a business focused on startups why would you not and so one of the ways we also thought about it was um did not know how to sell like my way out of a paper bag you know my joke is like prior to vanta the last thing i sold was girl scout cookies which is kind of true you're getting so you're like okay i'm gonna need all the help i can get But it would be really nice to have like a cohort of like happy startups to like experiment, inadvertently experiment on.
50:32You don't obviously want to, but you're like, I'm going to mess it up for a while. Might as well mess it up in a like bumper lane sort of environment than like off a cliff. That makes sense. So you apply, you get in and tell us anything like that was important from that three months and what you remember. Okay, to me, the structure of YC is, and I know I don't have this quite right, but is like week one, week one, week two, get your C legs. Like week three, pick a metric. And if you're B2B, it should be revenue. And if you're a consumer, it should be users. But like pick a metric and then pick a place where it's going to be in three months.
51:16Then do it, basically. and like show up every two weeks you know and tell people where you are where you tell people where you are and where you're going to get to and we call like the accountability scarecrow is you know you have to like um go tell someone you know oh i i said i would have 14 customers and i only have 12 but i feel badly saying this to you so i will have 17 next week right and you have to like do that and then at the end you have to stand up and like say the result and And you remember what it was like to be in that audience. There aren't many people who went through YC that had previously been in the audience as an investor.
51:57How did it feel to be up on that stage? Oh, totally bizarre. I bet. Totally bizarre. But did you make a lot of progress during YC? And I imagine you had a bunch of your batch mates using it. So we actually didn't because then no startup that small got us talked to at all. Okay. But it was YC companies that were like 50 employees. That was kind of the sweet spot. Okay. But you could easily say, I'm Christina from this winter's batch. Exactly. Which 100 % worked. And what I tell people now is like YC companies are just way nicer to each other than they should be rationally. Right? And it's just like, you send those emails, people actually reply.
52:38They might be like, thanks, but no thanks. But like, you'll generally hear something back. They might forward it. they're way more likely to get on the phone with you to talk than, you know, rationally they should. And just like that is helpful at every stage. Did you land any sort of big YC startup that you remember? I did. The thing that's honestly most salient is we so silly in that like first three weeks, you know, set a number and you're like, OK, well, there's basically nine weeks left. And I think I can tell two Vantas a week and they cost$10 ,000. So we'll be at$180K in March. cool ten thousand dollars they cost ten thousand bucks they cost yeah vanta cost no wonder none of your batch mates were uh signing up yes okay and like cool like that seems doable it was so hard but we hit it and i remember being like man i have like crawled across the finish line but like i might feel my head's at ease but like cross the line did you raise money at demo day basically yes did the did the um i think five or six days after yc the round was closed just talk to seed investors like no one who could write an a check because figured if we're gonna speed run this process like i don't want to touch a board i don't want to touch like it's not really a board member but it's gonna be like just just don't touch that with did you turn them away when VCs reached out.
54:07Were you like, no, thanks. We're not looking. We're only doing seed money now. So yes. And then the advice I got was, but like, let's meet the week after. Because like, you're in pitch mode. And you're kind of also like, you're like dialed at that point. But you want to be like, you want to show up and be like, hi, Series A investor. Great to meet you. I just closed a seed round in five days. Like, what do you want to talk about? Yeah. And so did that. did you meet the usv analyst at your day i don't know if they said some actually i think they said a partner at that point oh that's nice you know by the way fred wilson used to come to our demo days in boston i remember he was he wrote i was so psyched he like wrote maybe in his blog or something he remarked on how lovely the cheese plates were.
55:01Like I got these fancy cheese platters and Fred was like, the cheese platters are really, you know, good. But he used to come, bless him. So you raise, you quickly raise a seed round and you get back to work after meeting with the VCs and saying, well, let's keep in touch. Exactly. And you kept in touch for a while though, because I know for, I read that you did not raise a proper Series A until you were$10 million ARR. It's true. Nice. Wow. Nice. Like, again, the dream. Like, no one does that. That is so amazing. Before we go into that, I have a seed story from YC. When I was in the batch, this was when – there were not established norms about when companies started to engage with VCs.
55:54but it was all getting pulled earlier right but it was like NYC would be like don't talk to anyone but then you know the VCs were like sort of attacking and you know whatever and I think having seen that game I knew you just tell them you're too busy earning lots of money and closing deals and so whenever we get an email be like thanks I look forward to meeting with you you know maybe we can set something the day before demo day but like I'm too busy closing deals you know I was more polite, but like, hey, doing a lot of building, working with a lot of customers. Like, I look forward to talking to you at the time we will talk.
56:30See, you followed our rules. Like we say, if you want to be impressive to investors, you got to be making progress. And you're not making progress if you're meeting with them a month before dinner day. So I love that you did that. And I bet that made them more interested in you. Oh, 100%. Yes. Yeah, totally. 100%. So you closed them right away after demo day. Yeah. Okay. So then what made you decide to say, okay, I know there's some VCs interested, but we're really going to push them off until we're ready? For the seed round or the Series A? For the Series A. For the Series A. Yeah. So that was – it was actually kind of similar logic.
57:12and I think again confidence having like a pre I felt like a pretty good model of how early stage investors thought which was the business was working it kind of felt like again I could get I could find a founder get on a couple calls with them and like I don't know 50 percent two-thirds probability they would become a customer and so then you're like okay I have two hours should I spend it like walking to South Park and having coffee and walking back or should I spend it to getting a customer? And like the answer was kind of always get the customer. Yeah. And then, you know, you go to the VC and you're like, well, I have an extra customer, you know, like it was just like, and that will make them want to invest more, not less.
57:51Like, you know, my joke is like, they want to invest in million dollar series A's, error. They'd rather invest in two million error. They'd rather invest in three, like you are getting more, to the extent it works, like it gets more compelling, not less. But you've must have been really good at controlling your burn because from a practical perspective, yeah, what you're saying is obviously desirable, but sometimes you just need the money. You need to hire. So you guys must have been fantastic at managing your business. Yes. So I think there's two things. One was incompetence and one was more planned.
58:20The incompetence is we were just terrible at hiring. Like so bad. Why? So you put it off. No, it was worse. We tried. I think we were coming out of Dropbox that had very structured interviews and like structured rubrics for each interview and intense debriefs and just lots of stuff. And then we tried to do that, which like, I think actually kind of worked in engineering because we had a better idea of what we were doing. But for literally other, every other role, like I couldn't spell CSM. And so then I tried to construct this interview to like find a customer success manager. And it ended up being like seven stages.
58:58And again, like somebody had to go through an obstacle course. Yeah, it was just, and then we like, at the end, we're like, well, you got through the obstacle course, but like, what is a CSM really? You know, we just like did not. We were just like did not. We were doing a totally overcomplicated in it. And so hired really slowly. So there was that. Which is good if you're trying to control the burn, though. Hiring slowly. The other thing we did, which was more purposeful, and shout out Peter Reinhardt from Segment, is he had a blog online that had like five posts on it. You know, he'd like write a post every nine months.
59:33But they were all really, really, really good. and he had this like two-part series on like finance for startup founders and he had this post about cash and charging annually up front versus quarterly versus monthly and this like cash flow chart and I didn't totally understand it except I could tell that like oh annual is better and so selling Vanta for$10 ,000 at the time I just say oh yeah it's like$10 ,000 and like all 10 ,000 are due tomorrow, basically. And people are like, okay. And be like, okay. And so we, that's also how it worked is like we'd basically take the new business revenue for the month, pay people with it, and then like do that again and again.
1:00:17And the bank balance kind of stayed the same. But this is really critical because you reduced the friction by reducing the decision-making process. So customers didn't have to think, gosh, should I just get Vanta for a short audit or pay monthly? Or it was just one option, annual cost there. And the 10K, how confident were you guys in that number when you first threw it out? And how did you come up with it? Because it obviously was kind of like the right number. So when there was still a spreadsheet, I did take the spreadsheet around to some founders who'd seen it and said, okay, what is a reasonable price, an expensive price, prohibitively expensive price?
1:01:04And basically people said expensive was$10 ,000. Okay. But what's a prohibitively expensive? So that's kind of where we started. That's what I would think too. Like 10K doesn't like knock your socks off and feel like, oh, it's terrible. But it also feels like, okay, this is really going to matter because I'm paying for it. Like, yeah, I get that. That's really smart. Yeah. And then when I was kind of after YC, when I was selling a bit more, I would try to do the like, oh, if somebody doesn't blink, when I tell them the price, I'll tell the next person the price two times higher. But then I got a little scared and I started just emailing invoices and then people would ghost me.
1:01:41And, you know, you're like, you learn all that stuff not to do. But I was sort of like walking it up, trying to figure out where people would really oof. and the first salesperson I hired three, six months after that, I think kind of quickly realized and was more right, was like, I can play that game, but I have to go back and forth five times. If I say 10K, everyone just bails me money. And so he just said 10K and he was selling, you know, lower than I was, but he was closing four or five times as much as I was. And you're like, ah, you're better at this. So you continued to do your own sales for a while, it sounds like.
1:02:16I did the first$500 ,000 of sales. Okay. Yeah. Which I do tell, I mean, you know, of course you give advice that you feel like work for you for good or bad, whether or not it did. Um, but I feel like it helped cause you're like, and I would sell like a product manager for good and bad, but you'd like show somebody something and be like, well, what do you think? Like, would you use this? Would you use this? And I found it, I think cause I was telling to engineers that worked. And then I found that really helpful and like, okay, what should we build? What should we do? What do people understand?
1:02:44What do they not? I know we're coming up on the end of our time together, but I need to ask you about being a female founder, because you are up there on YC's leaderboard for successful startups with a female founder. And, you know, you're a role model, and that's a byproduct of your success, which is amazing. Do you feel like one? does it impact you or you do you ever think about that i mostly try not to honestly because i don't uh i haven't figured out how to channel that into something that feels like obviously helpful i do entirely wish there are more and it was less notable like my again i have a couple quips but one of them is like well more women should start an enterprise software company like it should be less notable um right right and like deeply that you know and again it's kind of a quip because it's easy to say and harder to figure out how to action.
1:03:42But I do deeply believe that. I, by the way, I don't think you need to channel it into anything other than doing what you're doing. Vanta is taking over the world and you are the CEO and founder. I'm going to like start to cry because it doesn't, it is, it doesn't happen every day. And, you know, YC has been around now for 20 years and there aren't a lot. And so like, I'm going to cry only because I'm so proud and happy about it, but just, just keep doing what you're doing. And that's how you're the role model, I think. Thank you. Well, speaking of keeping doing what you're doing, so you've been doing it for a little while and you're pretty young.
1:04:29And so, and we've talked about this with Paul, for example, when we had him on and he said, didn't he say, don't, someone said to him, And don't let this be the last cool thing you do about YC, right? So do you ever think about like what's the next cool thing I'm going to do? Or are you still too – like is it just too early to even think about that? I think too early. You know, I think people – I do get asked would you like start another startup? And yeah, I kind of give the like honest and somewhat incohate answer of like yes, sometimes I have days where you're like, man, if I did this again, I would like be so much better at it.
1:05:04or at least make like very different mistakes next time. And then sometimes I have days where you're like, this is really hard. And can I just go make art somewhere? And it doesn't matter if anyone likes my art, you know, there's no consensus. It doesn't matter. It just is art. And I don't know where I'd actually fall on that. Good. Because if you'd said there are all these other things, I'd be getting nervous because that would not be good for Vanta. for you not to be focused. Well, awesome. We will let you get back to running your company. Thank you for coming on the show. I think the listeners are going to love this one.
1:05:48Thank you so much. Thanks, Christina. It was great to chat with you. Thank you so much. Bye. That was so fascinating. And I just love her story. I hope the listeners find this fascinating because this is like a different entry into the startup world than a lot of the people we've interviewed. And like she taught herself to code in her 20s. I know. That's so cool. It's beyond cool. I wish that had been me. I know. I'm so impressed. And she's one of Y Combinator's most successful female founders. Well, and the other thing that she said early on that I just hope we all remember is how like having your boss say you're not the fake it till you make it type, I think is a huge compliment because it just means like you're genuine.
1:06:34You are not bullshitting anybody. You're really legit. And I think that's it. I think that's awesome. I think it's a huge compliment. And I wonder if she was saying, you know how she was saying she'd rather get another new customer than go meet with a VC. I wonder if that's because she had such great product market it fit that it's actually super fun to go through that sort of sales process. Oh, I'm sure. I'm sure that's part of it. Also, just like, I'm not going to sit here and tell bullshit about this product that I'm not done building, haven't sold enough of, waste my time having coffee. I'd rather just build it, sell it.
1:07:11Yeah. I mean, I think that's how genuine she is about this. I feel like if someone's like, what, how should, what do you think a good founder is? I feel like I'm going to point people to this episode because she did so many things the right way, even though it's tempting not to. It's tempting to do things like meet with investors instead of closing customers. You know, whether people want to admit it or not, they do it the wrong way. Yeah, I'm really glad we talked to her. Well, this is going to be a great episode and I can't wait for it to come out. Yeah, same. All right, Carolyn. I'll talk to you soon.
1:07:47Bye. music music music
From the publisher
In this episode of The Social Radars we talk to Christina Cacioppo of Vanta. Christina is a case study in agency. She actually did all the things founders know they ought to do but don't have the discipline to. She taught herself to code. She solved an unsexy but real problem. She focused on talking to customers instead of investors. She even put put off raising a Series A (despite inbound interest) till Vanta had $10M in ARR.
