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A
And at the time I emailed was christinasv.com and it was like the right side, that usv.com is way more powerful than the left side. And now you're giving that up. And so what are you, you're betting.
B
On the left side.
A
You're betting on the left side. And like why would you do that? And like what do you think will happen here? I feel like I could rule the world. I know I could be what I want to. I put my all in it. Like days off on a road less travel. Never.
B
I don't know if you know this fun fact. Do you know what you Katy Perry and Serena Williams have in common?
A
I've got nothing.
B
You're all on the Forbes self made women list.
A
I hate that list.
B
And you are ahead of them. Isn't that kind of amazing?
A
I would have preferred that list never existed. Yes.
B
You have that Midwest modesty.
A
Yes. Nothing good will come from that list.
B
Yeah, yeah. Those lists are. They're sort of made for the wrong type of people. Yes.
A
Or jail time later or something. Trevor Dewell had left that. I was never on 30 under 30 and I'm deeply glad about that now.
B
Yeah, that turned out to be an anti signal when I was thinking about this episode. The way I think about it is like where you are today is where a lot of people want to be. You have a company that's working, it's got like a cool startup name, it's got a cool office in San Francisco. Last valuation I believe 2,45 billion, but who's counting? Today you're at where a lot of people want to be. But if we rewind the tape to me, when I looked at your story, I think the through line for this is not counting yourself out. So I'm gonna put that out there. That might be true or might not be true. But the basics of it is you had a good job and you quit to try something new, to try to make it on your own, which a lot of people want to do, but they don't take the leap. You took the leap and it's not like it hit right away. And you created Vanta and you created this multi billion dollar company right off the bat you did like 35 things wrong or 35 projects that went nowhere. And I love that because I spent eight years of my life banging my head against the wall with failure after failure after failure. Each time believing this is the time, you know, let's start where you have a good job.
A
Yeah.
B
You have the job at usv which I think you kind of hustled your.
A
Way into, I would say, stumble. Hustled.
B
Ok.
A
I didn't like the stumble. Hustle, hustle. They announced that job like they do all their jobs on the Internet and said, hey, fill out this form if you want this job. Send us some links to your web presence. And so I literally sent them three links to my web presence and didn't email anyone who knew them. Didn't, you know. Turned out I, like, knew people from school who knew. Didn't. Didn't pull anything, just sent them links and put them in a form and was like, well, now I'll go back to making slides.
B
What kind of links?
A
It was Twitter, Flickr through the era of this. And I had started a design blog a couple months before and I lived in Berlin because I wanted to be like a designer who lives in Berlin, and those people seem to have design blogs. So I started one and that was it and they hired me, which is crazy.
B
All right, let's take a quick break because I want to talk to you about some new stuff that HubSpot has. Now. They let me freestyle this ad here, so I'm going to actually tell you what I think is interesting. So they have this thing called the Fall Spotlight, showing all the new features that they released in the last few months. And the ones that stood out to me were Breeze Intelligence. I don't know if you've seen this, but if you're in HubSpot and you have, let's say, a customer there, you can just basically add intelligence to that customer, the estimated revenue for that company, how many employees it has, maybe their email address or their location, if they've ever visited your page or not. And so you can enrich all of your data automatically with one click using this thing called Breeze Intelligence. They actually acquired a really cool company called Clearbit, and it's become Breeze, which is great because now it's built in. I always hated using two different tools to try to do this. Now it's all in one place. And so all the data you had about your customers now just got smarter. So check it out. You can actually see all the stuff they released. It's a really cool website. Go to HubSpot.comspot to see them all and get the demos yourself. Back to this episode. And I read something that was like, they, maybe Fred or somebody at the US V team was telling you, you should specialize in crypto. You should become a crypto vc. Is that true?
A
Kind of. It was actually. I was leaving, so this was end of 2012, I had a lot of angst because this job was great. They were great, you know, like, haven't you made it? And I'm sort of like, but I don't think I like it. And again, what's going on? And one of my hang ups was, you know, what have I done? Why would anyone take my money, right? Who's going to take a check from me versus, in my head at the time, Matt Kohler. This GP who's no longer a benchmark, but had this, like, illustrious Silicon Valley career of like, LinkedIn Facebook benchmark, you know, and you're like, me versus Matt Kohler. Everyone will choose Matt Kohler like a hundred out of a hundred times, which.
B
Is, let's say maybe a partially imposter syndrome, but also maybe hyperlogical. Also.
A
Yeah, I think, like, yeah, but, like, also true. Anyway, and I. I basically said that to Fred and he said two things, which. Or he said a couple things that deeply insightful one was like, well, you know, Gwen, Kristina, you've gotta, like, get over that. And you can either get over that by sort of out hustling people and like, kind of the fake it till you make it strategy. And you're sort of like, look, I've seen you in the office for two years, worked with you for two years. Like, you're not. You're not gonna be good at that, so you probably shouldn't try that one. The other strategy is pick something, go deep in it, and be the expert where no one else is. And in the fall of 2012, I recommend you choose crypto. Really good advice on a bunch of dimensions.
B
Right?
A
I didn't take it.
B
But, like, because you didn't believe in crypto or you were just like, that's not me.
A
I'm just like, I don't know if I want to be an investor.
B
Okay.
A
Even though it's great and it's wonderful and all these great attributes and like, everyone else wants to be a vc, but, like, I want to go make things.
B
So you decided to go make things. Take me back to that decision. Was that easy?
A
No. I was so angsty.
B
Was everybody patting you on the back and saying, you're going to make this happen?
A
Definitely not. What I did and what my plan was was I'd saved my bonus from the prior year, and it was kind of like a finance bonus, and I was going to live off of that as long as I could. So, like, no job, but a bunch of structure. Learned to code, learned to make products. Hopefully something would come out of that and very much pitched as that. It was not pitched as I am going to start a startup. It was pitched as I am going to teach myself to code. Because that's how I saw it and thought about it. And like, yes, I wanted to start a startup, but I'd seen over the two years at usv, so many people start startups to start them and then get into them and then be like, I don't want to work on this. But now I have people in office investor, like, I can't stop. But I think there was. I think people took that conservatism as, oh, you shouldn't be doing this. And so specifically, there was a. I mean, there was a bunch of, like, why no one leaves usv? Who has the option of staying? Why would you do that? Or don't you want to work at some other venture firm? Or, oh, you want to code. Why don't you go to grad school? Stanford has a great graduate program in computer science. Why don't you go work for somebody else? Because clearly you don't know what you want to do. And then some amount of, like, kind of the tougher stuff, I think, where one person in particular had been close to and who was very like, just the left side and the right side of your email address. And at the time I email, it was christinasv.com and it was like, the right side. That usv.com is way more powerful than the left side. And now you're giving that up. And so what are you.
B
You're betting on the left side.
A
You're betting on the left side. And, like, why would you do that? And, like, what do you think will happen here?
B
So you have the good job.
A
Yep.
B
You quit. You hear the look. You took the rights out of the email, which was the powerful part. You threw it away. You're betting on the Christina part, of which there are many, many. And your plan is not even to go start a company. It's to learn how to code. And you're going to teach yourself how to code by going on online and learning how to code that way. And my understanding is that worked because I went to your website. Well, you have this, like, list of projects on purpose. I built all these things. Yeah.
A
None of which you've heard of.
B
Yeah. Mostly went nowhere. There's something romantic about that, too. Like, I'm gonna go in a cave and I'm gonna reinvent myself and learn this magic superpower, and I'm gonna train in the mountains where nobody's looking. And then I'm gonna come back stronger.
A
Yep.
B
It may not have felt that way.
A
At the time, but it, like, I kind of knew I was supposed to feel that way. And then day to day, there was some men of, like, I spent more than my, like, daily cash allowed, you know, but, like, I kind of knew that's what I. A better version of me would feel. But practically, I knew I was a person who benefits from structure and isn't always great at doing for myself. So what I did was a friend of mine had just sold a company to eBay, New York, and opened up this. This big space in New York that was actually right across the street from the US V. Office. And so I got up every day and I got dressed for my job, and I basically walked to the same place, but I went in a different door. And then I sat with those engineers and they drew up.
B
Did you actually dress up, by the way? Because I feel like they're psychologically subject to actually dressing up. Like you're going somewhere.
A
Yeah, I mean, tech dress, but it was like, I did not wear pajamas.
B
Right, right.
A
Like, yeah, yeah. And then I'd go and I'd, you know, show up in the morning and I'd, like, do my Udacity tutorial or Try to understand JavaScript to varying degrees, and then, like, go home at, you know, 6:00pm or 7:00pm and then often, like, keep doing stuff. But basically it was like, tricking myself into acting like I had a job so that I got up every day. I was there by 9:30. You know, I was just doing the things. And I. And I do remember there was a time my family took a vacation that I went along with in January, and I came back tan. And everyone was like, where were you last week? Like, basically, like, why weren't you at work? Why are you tan? And I would be like, I'll campaign for this. You know, like, I'll chop. Everything is PTO to me. Um, but it was like also a. Like, oh, yeah, I got this. Like, that's. That was kind of like a fun, Fun moment too.
B
Yeah, I like that. So you have this era, which is kind of like in the movies. It's the montage. They just fast forward through this part takes two minutes, even though in real life it's two years. And you have this thing written on your site that I love this quote. And I think in my research, this was my favorite thing I pulled from you, which was at the top of your site. It says the function of the overwhelming majority of your artwork is simply to teach you how to make the small fraction of your artwork that soars. And this is from a book called the Art of Fear. Can you. I love that. Can you explain that?
A
Yeah, I think it's deeply driven creative projects, and I think startups or businesses or Internet art is like, they're all creative projects. One thing I learned at usv, seeing. Seeing people bitch, but then, like, hearing the stories behind their big, you know, Tumblr, Twitter, Foursquare or whatever all the big successes of the era were. When I walked into usv, I was like, everyone is Mark Zuckerberg. Not actually, but, like, everyone. You know, like, startup founders are people who have an idea visionary, and they go into their room and they build it, and everyone uses it, and it's like the first or second thing they've done. And, like, Facebook bigger. But that was kind of all of Mark's projects. And so, like, that's the way, you know, and, like. And I'm kind of like, shoot. I'm like, not. It's never worked for me, so I'm probably not one of them. And USV was just so helpful in disabusing that notion and being like, look, some people, like, a very small number of people can do that, and that's incredible. I wish I were them. I'm not. Most people actually try a bunch of stuff and eventually something might work, but it's like, at best, Thing 5, and it might be Thing 55, but no one really talks about that because it's both. Because it's, like, painful and kind of not fun. And, you know, it's supposed to be romantic, but actually just kind of sucked. And I'm, like, hungry for two years, literally and metaphorically. And it's so much nicer. Like, you get so much praise for sort of being, like, the brilliant person. Right? And that's the expectation, too. I think. I just had a like, well, yeah, but, like, that's discouraging so many people from starting.
B
It's sort of like when you watch a bunch of movies about love, and then you're like, this is what it's like. Yeah, I will bump into a stranger. Our papers will fall on the floor. We'll swap a paper. We'll swap a paper. He'll have to come find me, but then I'm not into him, but he just pursues me anyway. And it's like, if you have that notion that that's how it goes, you'll almost count yourself out of other things that could have worked otherwise. If you watch the social network, you're like, that's just how it is. Brilliant. Genius has. Has a vision. Does it takes off, and then he rides that bull at the rodeo. We actually, after I read this quote on my team, we started using this phrase just called bad art. So I'll hit up my team in the morning. I'll say, hey, let's make some bad art. Like, intentionally, just almost lower the stakes. Instead of, we have to find the next big winner idea.
A
Right.
B
Let's just make some bad art today. And the analogy I gave them, I said, imagine, like, you know, you go to a hotel or a motel. You're doing something. You're going to a place that you've never been before. Maybe nobody's been there before. When you turn on the tap, like, it's muddy water at the beginning.
A
Yep.
B
And if you look at that and you're. It's like you're mortified by it. It's disgusting. You'd turn it off right away and be like, ew, bad.
A
Right?
B
Leave. But if you know that actually that's the process that you sort of have this muddy water of bad ideas and bad skills at the beginning. Get it out of your system. Then suddenly the water starts running clean. And I think that framework is just very useful for anyone who's doing either creative endeavors or startups, which are a pretty creative endeavor too.
A
Do you know the story about making pots?
B
No.
A
From the same book. So. And I think it was, like, around the chapter where that quote was. But anyway, it was an art teacher, and he said, okay, art school pottery class, you have one assignment all semester. You have five weeks to make the perfect pot. You can turn in as many pots as you want, but I will judge them all. And the highest grade will go to the person who has the best potential. And student one spends all semester crafting the perfect pot and hands it in at the end. And student two makes two pots a day, and they're all bad for a long time. Right. But over the course of the semester, it hands in whatever, like, 300 pots. And, like, who gets a better grade?
B
Of course. 300, right.
A
Yeah. Yeah. But it's like that concept, it's, like, so true.
B
And you have to live it almost to really internalize it.
A
Yeah.
B
Actually a great thing I did once with my company. There's. You've probably seen, like, the marshmallow test, like, the psych test with kids. It makes a good point, which is you give a bunch of supplies to. You break your team into a bunch of groups, groups of maybe four or Five. And they get, like, sticks of spaghetti, one marshmallow. And there's something like maybe a string and like, two other things, like a piece of tape. And so the idea is, hey, you have an hour. At the end of the hour, I will come around, I will measure whoever from the tabletop has the highest marshmallow. So whoever could build the biggest tower wins. And what most people do, what my team did, and everybody who does this the first time pretty much is you immediately go into, like, the way we do most things in corporate life. So it's kind of like, okay, you're in charge. You do this. You sort of segregation of duties. You start trying to, like, plan, and then you. So you sketch a little bit. Then you start building the tower. And at the very end, you're like, okay, okay, it's almost time. Put the marshmallow on. And the entire thing collapses. Because even though a marshmallow looks so small and, like, light compared to spaghetti sticks, it's way too heavy. And you don't realize that. Cause you didn't, like, you, like, backloaded the possible failure, you know, the failure mode or the sort of test of the idea. You spend all your time kind of planning and architecting this brilliant, beautiful thing. And the cool thing that they've shown in this is that when they do it with kids versus adults, the kids right away either eat the marshmallow or put the marshmallow on right away, and they're like, oh, it's too heavy. You have to have, like, five spaghetti sticks to hold this thing up. They figure that out right away. They don't kind of save that to the end to try to perfect it.
A
Yep.
B
And that sort of iterative thing about testing the riskiest assumption is maybe important, it seems like, for you. Did you make that mistake of kind of, like, overanalyzing over planning at the beginning? Like, not testing with customers?
A
Less the very beginning. Because at the beginning, I was just Bill. I built a book website. It was like Goodreads, but better. But it was actually worse because I didn't know what I was doing. And. But, like, it was something for me. This confused everyone else. Right. Because they'd be like, well, you're. Well, not, you know, what are you doing without having a job? And I'm like, I'm building a book website. And they'd be like, are you going to compete with Amazon? No. Like, are you going to compete with Goodreads? And you're like, well, you know, with my. With my friends. But like, no, you know, and then they'd be like, well, what would you say you're doing? You know, and you're like, mostly battling JavaScript errors, trying to. And like spending a lot of time on stack overflow, you know. But anyways, it's like whole confusing thing. But the beginning, it was just I, like, like when I would go visit a friend's apartment, I'd always like, be drawn to their bookshelf. You want to see what's on their bookshelf? Anyway, so I was like, okay, what if I can get everybody's books online? But he was like, clearly this is not a business. Like, best case, I'm making like 50 bucks a month, you know, Amazon referral fees. Like, not a business.
B
But you did it anyways. Why?
A
Because I wanted it. I want. And it was a good. It wasn't. You know, like, you do their initial coding tutorials and you, like, are making whatever the other person wants to make, which is not what you want to make. And like, I actually wanted this and it like forced me to be like, oh, you know, now I want like an animation when you shelve the book so you. Right. And then you'd like, learn about CSS animations, whatever it is.
C
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B
And so you. So you started building stuff for yourself.
A
Yep.
B
Did you ever switch gears to, okay, now, now I'm going to do the startup startup. I'm going to do the thing that might actually, you know, get me out of poverty, like self induced poverty, basically.
A
So at that point I was very like, look, I, you know, just taught myself how to code and like, you know, am I that good? No. But learning how to do some of this is much harder than it should be. And a lot of it's because our programming tools make us hold everything in our heads. And you have to teach yourself to think like a computer and read through code, which is not how a person think like a computer. And once you have that, everything gets easier. But why we are typing on computers. And so I kind of got on this. If we could make our programming environments better, they will just make more sense and more people will learn to code. And so I was really into that personal problem. Also, the live in the future and build back, you know, whatever. All the, all the startup trope advice.
B
I'm curious about that. What startup trope advice actually helped you?
A
I think the build something you want is a bit of a red herring. It works in some cases, but you're also very limited to your experience. It's kind of like when they tell writers, write what you know and then you like, you know, it's like a 14 year old who's had a charmed life and like they just don't know that much. And so like, what are they gonna write about? And so my version of that is like, look, if there is something personally meaningful, like by all means, go for it.
B
That's top ranked.
A
Totally. But like second best is like, find someone else with the problem and deeply, deeply understand them. I think there's a ver. The shut your eyes, imagine the future. What's it look like? Build that. I think this makes sense in retrospect. I think in the moment it's pretty hard to generate reasonable startup ideas during that.
B
Right.
A
But I can tell you a story about Vanta or Vanta fits that. And it does, but it's.
B
But that's in retrospect.
A
Yeah.
B
So what was the actual in the moment way that you stumbled into this idea? Vanta, that now seems obvious, as all great ideas do once they exist. And now there's you guys and some competitors trying to do the same thing. But that was kind of a novel idea and it was a new part of the market at least. What was the insight for that?
A
The insight was wanted to start a security company that started serving startups. There seemed to be like security with this huge market, but no one was really focused on startups and sort of didn't use security tools. And I was sort of like, why? And like when does this become a 90 quadrillion? Like go from a 0 Tam to like 90 quadrillion market size in precise terms?
B
Yeah, that's the official number.
A
Yeah, exactly.
B
But wait, why security? Because like, you know, when I'm talking, I've been talking to you for, I don't know, 20 minutes now. You don't strike me as somebody who's like, I wake up every morning and I was thinking about security during that year off. Why did you even think about security to begin with?
A
It seemed really interesting. It seemed like this kind of competitive cat and mouse thing where they. With attackers, where there's like kind of a real dashboard.
B
Right.
A
I think one of the things I've. I mean, I guess I knew, but I didn't really know. Like, I'm very competitive. Should have played more sports as a kid. Didn't through Vanta have an outlet for a lot of that energy? Which is great. And I think honestly when I was at Dropbox, I worked with this product security team and they were great. They were super fun and they were really good educators. And it's not like they'd hosted seminars on things. It's just like they wanted you to fix something, but they'd come over and sit next to you and explain why it was important and how and all the. Anyway, they were just great. And so in coming up with startup ideas, there was a bit of like, well, this actually seems like a deep enough, interesting enough space that if I work in it for years, there'll be lots of things. And if I can't come up with anything and end up burning 18 months of my life learning about security on the Internet, could have been worse. Right. Like, you kind of look back and be like, okay, worst case, nothing comes out of this. But like, I, you know, I'll feel as good as I will or will.
B
Play the dots for me. So you, you took the year or multiple years off to teach yourself. Two years.
A
Yeah.
B
But then you go to Dropbox.
A
Yeah.
B
So you go back to getting a job.
A
Yeah.
B
So I feel like we, like there's a part of the story that's like, I iterate. Iterated. Finally I found it. No, no, no. Finally you found a job at Dropbox?
A
Yeah. Cause I was kind of like, okay, now I can code. But I've never had a real job. I've never worked at a company. I've never worked with people. Also, my friends are kind of getting promoted and I can. It's unclear if I'm employable. This seems bad. And I was really frustrated because again, I wouldn't tell people I wanted a startup to come out of that, but I did. But I also at the time was like, well, nothing I've worked on should be a startup. Right? Totally.
B
Yeah. So what was that story you told yourself? So you spent the two years you bet on yourself, which sounds amazing. That's a great T shirt. Bet on yourself. But the reality of it, I do it for. I told you, I did it for eight years. And I was delusional enough to keep going. But also, objectively, it was bad and I should have. I had to tell myself certain stories in order to either keep going or to just maintain a sense of confidence beyond that because the evidence was telling me, you suck.
A
Yeah. Yeah.
B
And I just couldn't tell myself, you suck because then I definitely suck.
A
Yeah.
B
What were you saying when the evidence kind of said you suck?
A
This is very silly. I had this, like, survey I would fill out a Google form. I'd fill out for myself every Sunday or every weekend. What are you working on? How do you feel about it? What are you going to, like, what's your next goal? What are you going to do to move forward?
B
You made that for yourself?
A
Made it for myself. It was like a personal accountability thing. Right. And I asked a bunch of questions. They were all useless. The only question that ended up mattering was what would make you stop working on what you're working on right now? And to your point, it turns out my present self always thinks I should keep going, but my past self sometimes thinks current self should stop. Right. And so it was actually like, looking at those answers and being like, two months ago, I should. Said I should stop. If I got to the point I'm at now, I don't actually think I have countervailing evidence. I just have stubbornness. Shoot, I should probably stop.
B
And so that's how you were stopping those projects. I sent you some questions ahead of this to try to understand what you think is important to talk about. What do you think is insightful? You said something that I really resonate with, which is managing your own mind, managing your own psychology is one of the most important things. How does one do that? And what's like, how would you teach that to somebody else? Or how would you talk about that to somebody else?
A
It's, I think, hard to do, hard to teach. I think what I try to tell people is figure out what, like, it's personal and not personal sensitive, but like personal, like specific to you. And figure out what makes you happy or centered, whatever those things are, and like, do not give them up. And so for me, for years it was like a, you know, running three or four times a week and like exercise, sure. But it was actually just like the mind clearing catharsis, kind of meditative, like running. And, you know, it was like running for me, but like, whatever for someone Else. And it's like, whatever that thing is, do not give it up. And I don't care how busy you get, but sort of know what makes you feel like you. And don't drop those things.
B
Know what things make you feel like you. Which is kind of like what you're talking about is habits and hobbies. Is that more of what you're thinking about?
A
It's just like that feeling where you, like, you're, like, moving through the world and you, like, feel like you're at your best, you know, like you're the best, shiniest version of yourself. It's like, what brings that on?
B
So for you, running as one. What else?
A
Running was one reading. Like, not in any. I mean, kind of in elegant, intellectual way, but actually just because it is something I have done since I was six years old. Right. And so, like, if I think of, like, hobbies or anything I've done through my life, reading is actually one of the biggest through lines.
B
Right.
A
And so there's a part of that that just feels like me.
B
Yeah. Cause I was looking. You read like, I don't know, like, 30, 50 books a year or something.
A
Yeah, but it's. It's like. I mean, yes, and I wanna learn things and like, blah, blah, blah. But actually, it's just like, it is centering.
B
I feel like I do that when I was running a company. And by the way, mine was not a 2.4 or $5 billion company. I was like, I have no time to read. Are you kidding me? There's problems everywhere. I'm drowning in problems. And did you just replace TV with reading or something?
A
As simple as that? Yeah.
B
Like, actually, Eric told me that you are, like, extremely quick with reading. He's like, she would take a bus to work.
A
Yeah. And read the book.
B
And read the whole book on the bus ride.
A
Yeah. I mean, over the course of a week or so. But, yeah, like, actually, to this day.
B
The way he said it was more legendary. He was like, nah. To and from COVID to cover.
A
No, that wasn't it.
B
She rolled that.
A
I actually still take a bus to work. Part of it. So I can just sit there and like.
B
You bus to work?
A
Yeah, because look, if I take a car, I'm just going to, like, sit in the back with my laptop writing emails, you know, and in a bus, like, I want San Francisco bus. I'm not pulling on my laptop on that unless something's, like, really gone wrong. And so it just forces me to, like, sit there and have 20 minutes between home and work.
B
Right.
A
And I like that much more.
B
You know how people are, like, obsessed with cold plunges?
A
Yes.
B
I think the more hardcore version is take a San Francisco plus to work. It's like, wow, you can endure a 18 minute bus ride with like, the buses aren't bad.
A
5R used to be my bus. Five hours are great.
B
I used to take the 38. And the 38 is like an actual zoo. It's like it's. Anything can happen.
A
Yeah. Yeah. No. 5R. Great bus. I miss it. I miss it.
B
Okay, so. So Banji neuropsychology said, figure out what makes you feel like you most you and make sure you stick with those things. Keep doing those things. It'll kind of keep you centered with it. What about manage your own psychology when it comes to self doubt when it comes to getting down on yourself? Because I spent two years. I didn't really land where I wanted to land with it. Did you have a conversation with yourself there or a story you told yourself in order to.
A
Yeah, I was so annoyed. I was. Which in retrospect, I was like, being so pretentious. Like, life was good. You know, again, like the Batna. Like, my worst case outcome was becoming a product manager at Dropbox at the height of Dropbox's power. Like, my life was great.
B
Could you just say the Batna?
A
Yeah, right. But like, my life was great. It did not feel great at the time. It was totally great. And again, I knew. I was like 5% aware of that 10%, but that was not the lived feeling.
B
Do you use negotiation terms like that just regularly?
A
Hopefully not. That sounds kind of obnoxious. I'll try not to now.
B
No, I like that. I've always felt that if you build a great Silicon Valley company internally in your company, you should be a totally normal person, but outside, you should have that like, 10%. Crazy. Yeah, it just gives you, like actually like 2x the valuation. It just creates this extra aura. Totally true. Wow. She's. She's barefoot all the time. Why? Oh, interesting. She must be one of those real outlier types.
A
Oh, my gosh.
B
All right, I want to ask you about this list of ideas that you did. So I've looked back in my career and even when I went through eras where I tried something and it didn't work, a lot of the times I look back with the benefit of hindsight now, and I think, oh, I was just sort of an idiot about it. Had I actually either stuck with it or done it differently or pivoted the market, that actually was a good Idea. I'm curious, do you feel that way about any of the projects you worked on?
A
Like, they're art projects, and I say that with deep love, but, like, they're not businesses.
B
Okay. The voice assistant for biologists. Yeah, that doesn't sound like a great voice.
A
That was just comically bad. No. Yeah. There was, like, a deep lack of any commercials in nearly everything on that list, which I think is part of why Vanta has had commercials like, baked in from the very beginning, because I'd made that mistake so many times.
B
What about now? So if you weren't doing this or in general, like, when you operate a business, you see a bunch of pain points, blind spots, maybe like parts of the market that are unaddressed. If somebody's listening to this right now and they are looking for, you know, inspiration or ideas that, you know, spark thoughts in their head about stuff that they could go do, where would you look? What would you recommend people think about? What problems do you think need solving?
A
Yeah, I think so. So much of what I think about that's not kind of directly in Banta's wheelhouse is something around, like, running a B2B SaaS or being in a B2B SaaS business. Forget running it, just being in it. There's like so many, like, someone please fix the go to market tooling stack. There's 9,000 tools and none of. And it's like you jerry rigged them together in this Rube Goldberg machine and the marbles are all up on the floor. And like, if anyone wants B2B SaaS, just, like, fix that, go full stack on all that. But for people who don't want B2B SaaS, of which there are hopefully many, I think the process Vanta came out of, I mean, I of course, like. I mean, I liked it going in, but now, of course I really like it. But that was. Pick something you want to learn about and just go talk to anyone you can about, like, what their days are, like, what their problems are, like, just, like, what's going on and kind of try to develop a mental model of this space.
B
The story I heard about Vanta, which sometimes we make up these retrospect stories, so I don't know, you tell. You.
A
Can I try to actually tell that the true one?
B
Like, blink twice if it's true.
A
Yeah, whatever.
B
But it was. You're at Dropbox, you work on this thing called paper, which was this. I remember, like, seeing paper at the time was like this idea of this, like, collaboration tool.
A
And you go to one of Google Docs?
B
Yeah, Dropbox is Google Docs. You go to launch it and it's like, hey, we don't have Sock too, so can't really launch or customers can't use it. And you were like, sock, what?
A
Yep.
B
And you didn't know really what that was. And you were like, so how do we get that? And you started asking questions to try to understand, like, what is this thing that blocked us here? If it blocked us, maybe it blocks other people. Dropbox had a security team that was going to be able to try to solve those problems, but the average startup doesn't. And the next part of the story that I liked was, even though you had just spent two years learning to code and built 35 projects and coded them up and shipped them out there or whatever, you didn't write code for this. You were like, I'm going to test this idea with an Excel spreadsheet only.
A
Yeah.
B
And you went to one or two startups, I think YC startups that you thought might need this. And you were like, hey, if I did this for you, would that be valuable? And they're like, oh, yeah, sure. Can you. How much of that is true?
A
All true.
C
So here's the deal. I made most of my money from a newsletter business. It was called the Hustle, and it was a daily newsletter at scale to millions of subscribers, and it was the greatest business on earth. The problem with it was that I had close to 40 employees and only three of them were actually doing any writing. The other employees were growing the newsletter, building out the tech for the platform, and selling ads. And honestly, it was a huge pain in the butt. Today's episode is brought to you by Beehive. They are a platform that is built exactly for this. If you want to grow your newsletter, if you want to monetize a newsletter, they do all of the stuff that I had to hire dozens of employees to do. So check it out. Beehive.com that's behive e e h I v dot com.
A
The stylized part is all the Dropbox stuff happened. There was no light bulb. I was like, not smart enough to have a light bulb go over my head at the end. Wish so. But it was just like, learned about the whole process, learned what it would take, and then, like, basically ran screaming from the room because it just sounded awful. Especially when we were trying to launch and even figure out if we had product market fit to the idea of, like, we're going to go two years of work to then see if we have product market Fit. You're like, bad, bad. Like, how do I find reality faster? Came back to it later, did the spreadsheet thing. And I think, honestly, it's like, because there's 35 things on the list, like, kind of at the point where you're like, okay, I can write, you know, maybe someone's shoddy JavaScript, but, like, I can code the thing or code a first version of the thing. That's not the hard part. The hard part is, does anyone want my thing at the end? And so, like, how much of the validation can you front load there?
B
So I think a lot of people hear that and they're like, they hear you should talk to customers. You should validate if people want this, make something people want. Yeah, I don't think anyone has any idea how to actually do it. So what is the quick and dirty recipe for how you actually go? Who do you talk to? What do you really ask them? How do you make sure you're not getting these false positives just by being like, eager beaver? And they're like, yeah, that would be. Maybe I'd be interested. And you're like, they totally loved it. Yeah.
A
So on the false positives, anything that is not, can you do this for me now, tomorrow, next week is a no. And people are really kind and they want to be kind. And so they don't say, like, rarely do they say no, but a lot of like, oh, maybe next quarter. Like, I don't need this, but my friend might. Hard nose.
B
Yeah, you should date my friend.
A
Totally hard nose. I think on who to talk to. I mean, look, we started with, like, anyone who would talk to us, and then it was just like. And then so it ended up being co workers, former coworkers. Because you had, like, some like, Well, I don't know if you know anything about this topic, but you're kind of a nice, ish person. And so I'll, like, give you a half an hour sort of thing and then just fan out from there. At the end when they're like, well, you know, you ask them, do you have anybody else? And they would list people and, like, say, yes. Follow up with customized emails. They could forward, you know, like, make it easy for them and just keep going out.
B
Yeah, I think that's an important one. Make it easy for them to do the thing they said they want to do.
A
Oh, yeah, like, follow up and be like, thanks so much for meeting me. Like, I would love to talk to your friend who, Eric, who said this. Like, here's what I'm Working on like. And just like, assume they will, like, write them an email they will forward.
B
Exactly. So you. Have you ever read this thing called the Mom Test?
A
Yes.
B
Do you subscribe to that?
A
Yeah, generally.
B
Yeah. They. That was helpful to me when it was. There's only. I don't actually remember what was in the book. Only one line which was, they can't tell you about the solution, but they can tell you about their problem. So all your questions need to be first about their problem. And then at the end, if you want to ask them about your solution, great. But just assume they don't really know what the solution needs to look.
A
Yeah, I think that's true. Try to avoid yes, no questions, which is harder than it sounds. And there's a bunch of kind of user research tips, tricks of like, if somebody mispronounces something, go with their pronunciation. Otherwise they're going to like, don't break rapport. Exactly, exactly. Like, a lot of.
B
I think I do that and it sort of is like a problem because it's kind of a know it all move.
A
Right.
B
And then it makes them feel like their mind goes over there.
A
Exactly.
B
Oh, am I. Am I being stupid? Did I say something stupid?
A
Exactly where you just, like, want them to, like, stream of consciousness at you, basically.
B
Yeah, exactly. Do you have any good Hustle stories for how Vanta kind of got the flywheel going? Because, you know, startups don't kind of like explode right away necessarily.
A
Yeah.
B
And I've seen your, like, ARR chart, which looks like a beautiful hockey state.
A
Yeah, totally.
B
But if you zoom in, it's like, wow, that was a year where it's like, pretty kind of small. And then, then it started to accelerate. Was there anything you did that you thought was interesting, unique, that kind of took hustle, creativity?
A
It's so funny looking back because, like, I sent a bunch of outbound emails to YC companies, but I didn't know the word outbound at the time. Right. I was like, emailing YC founders for feedback and I legitimately did want their feedback kind of to this, but it was like half a. Like, okay, I'm going to spend, you know, 60, 70% of the call talking about the problem and how you're solving it. And then the end be like, I am building a thing. Would you like to hear about it? But it was like, totally cold. Outbound. You know, I just like, didn't know that word.
B
So you emailed a bunch of YC people that got the ball rolling. What happened after that?
A
Honestly, the early Strategy was like just do and try everything and then see what works.
B
So what did work?
A
The outbound worked. There was a word of mouth. We tried actually really hard in the early days too. Basically build this call response in like founder Slack channels or VC Slack channels, where someone said SoC2 and someone else would say vanta. And you just wanted this, you know.
B
And how do you do that? You're saying, like, build the brand in people's minds.
A
Yeah. And that was great for a while and then a bunch of knockoffs came and there's a bunch of other ways to get socked to. And so that association.
B
I remember you guys had the billboard. It was like, what is it? Compliance. That doesn't sock too much. Yep. Still up. Yeah, that was good.
A
Still up. Yeah. I joke with people, like, we make software, but like we also make a billboard and we're equally known for both. Equally as important. What else podcast advertising really worked in? I mean, actually it still really works, but like really worked. In the early days, I thought podcast advertising was just gonna be like sending money out the window. I was totally wrong.
B
And that's what happened. Somebody on your team pitches you this. Eric pitches you.
A
Eric was like, I want 20k to go on Twitt this week in startups or something. And I like rolled my eyes and said, fine, whatever, go. You totally were. She was totally right.
B
Eric is like this mythical figure to me now where I've only ever heard great Eric stories. And so I don't want to hear any. If anybody has a bad Eric story or an idea you had that didn't turn out true, don't tell me, please.
A
No.
B
All right, I want to ask you about a couple other of your controversial or maybe just less consensus opinions. I've seen you write these somewhere on the Internet. You tell me if you still believe these and why consistency is overrated. This is on your website.
A
Oh, yeah. People read a lot into this. I'm just like joking with myself because I say contact me through these four ways that all have totally different names on them.
B
Oh, okay.
A
It's just like minor naming consistency. Yeah, it's this minor self awareness thing that I think people think is meant to be a broad philosophical statement. Do I actually think it's a broad philosophical statement? No, probably not. I think Vanta's taught me consistency is actually underrated.
B
Yeah, I was gonna say you strike me as somebody who's consistency first. Yeah, it's bad when the goalposts move. I don't know if you're saying you think this or that other people think this.
A
I think other people. The advice tends to be, right, like, you know, if your goal posts keep moving, it's hard to find happiness. And, like, you're always pumping out explain what it means.
B
So, like, what does that even mean?
A
The goalpost moving? Like, I think, I mean, gets bought in lots of forms of life, but, like, let's take startup founders just because, right? It's like, you want to start a company, you want to hire some people, you want to raise a seed round, you want to get to like a million nar, but then by the time you get there, you're like, actually, I want to get to 10. Right? Yeah, yeah. And there's like, always something you are chasing, and I think that it's generally seen as a recipe for unhappiness. Right? Like, why can't you be happy in the moment? You've done this thing prior you thought was great. Like, why can't you think it's great? And I think that can be true in some cases. But I actually think, or I think that the trick is slash. Downside is if you're only happy when you hit a goalpost and then you're moving them, you'll never be happy if you actually just like the work. That's what it doesn't matter. And I think a lot of things are more sustainable when you like the work, especially when you have a lot of work to do.
B
My formula is progress equals happiness, which is that no matter where you are, it's sort of like the Y intercept doesn't matter. The slope matters. And so wherever you're at, if you don't feel a sense of progress in your life, you will feel unhappy, and then you'll feel even worse. You'll feel guilty for feeling unhappy because you're like, I guess I do have all these good things in my life, but I still don't feel this way. I'm just fundamentally broken inside. I'll never be happy. When in actuality, it's just a sense of progress. Even better. A sense of progress in a direction that you have set out intentionally, that you care about.
A
Yep.
B
Um, and I think that in that sense, moving the goalpost is great because you're saying, I would like to continue making progress. I enjoy progress so much. I. Why would I stop my progress? That stops my happiness. Yeah, it's a different way of looking at it.
A
Do you remember deep cut 10, 12 years ago, Jess, who that founder of Polyvore at the time, now Sequoia, wrote a blog post about founder Psychology.
B
No, what did it say?
A
It was like, why? Basically like, why are founders always unhappy? And she's like, especially when their companies go like this. And it was a line up into the right. And she's like, because if you zoom, you know, again, Y axis getting higher, like what is this? Because if you zoom in on the graph, it doesn't look like a, you know, 45 degree angle. It looks like a roller coaster that is going slightly higher. Right, right. But it's like the roller coaster along the way and like, you know, again, even when you zoom out and you've got this lovely 45 degree line, the downs hurt every time.
B
Yeah, it's the peak to trough that you feel. You don't really even recognize that you've gotten higher progressively each time. You also have another one which is high standards are bad. You think that in generally people don't say this, but they imply it in different ways that don't have such high standards. What's the situation where that's come up for you or you've felt that?
A
I think a lot of Vanta stuff and I think within the company and then with, you know, kind of partners or folks outside and I mean some of the feedback we get that like I kind of, I don't appreciate more than anything else is like people care, people respond super quickly. Like, you know, again, something might have gone wrong, but the person tries really hard to fix it. Right. And I think those things definitely don't happen everywhere by accident. Not to say I had, I mean, hopefully a small role in it. But I think when people join, there's a little bit of like, oh, the bar is here at Vanta, like kind of scary. Did I join the right place? Like what's going on?
B
What's an example of that? Where would somebody feel that?
A
A couple places. But I guess in go to market our expectations around quota, around attainment, they're way off industry, they're way higher. And I think if you just, if one just hears them in the, in a vacuum, they're sort of like what is what? Like why would I, why would I sign up for that? Then they join and it's like, oh. Cause you're surrounded by people who are like into what they do, getting better every day, want to get better every day, care a lot. And that sort of environment can be like really infectious.
B
I'm curious, did you ever read this leaked production document from Mr. Beast? Did you ever take a look at that? Did you see that going around like a few weeks ago?
A
I know you Don't. Yeah.
B
So, like, right around the same time that Paul Graham put founder mode out there, and everyone was like, oh, founder mode. Like, but wait, what is it exactly? And like, you know, it was like, I think, yes, but what? Part of a lawsuit. Mr. Beast's like, internal doc. He wrote for his production team, leaked a big part. Like, we've gotten to know him and become, you know, pretty friendly with Jimmy over time. And it's just stunt. Like, the number one thing. You go hang out with Jimmy for a couple days. Like, you walk away and you're like, oh, he. That's what people. That's what it means when people say reality. You know, Steve Jobs used to have this reality distortion field.
A
Yep.
B
And it's. And literally, he. He. His company is based in, like, a tiny town in North Carolina. So like, he gets people to move there. And then once you're there, you're in his bubble. And in his bubble, the expectations of what work is about, what success is about, what we're able to do about the timelines. We do them on about what it means when something says, no, not possible. And he's like, one of his things. Like, push past the no. He's like, you know, you have to be able to push past the no. You don't always have to get it to be a yes. But, like, if you just come back and you said, oh, we, you know, we asked for the permit and they said it's going to take six months. And he like, that can't be the end of this story. And we saw it on every little thing. Like, for example, we wanted to play basketball the next day, and it was midnight, and somebody was like, oh, man, I can't wait till tomorrow. Like, I just want to play. And he goes, well, why do we have to wait? Like, well, it's midnight, Jimmy. What are you going to do? He's like, I'm sure there's a gym around here somewhere. Let's go find one. And we're like, yeah, but they're going to be locked. It's midnight. Like, schools aren't going to be open because they call the athletic directors. He's like, just call. Call all of them right now in the county. It'll take us 20 minutes. And offer any of them a thousand bucks if they'll come open it. And, like, part of it was like, oh, he just throws money at every problem. But actually, it's not about throwing money at it. It's. Yeah, everybody else would immediately just default to, like, does not possible, not feasible. Not. Not going to be doable. Whereas his default assumption on any given thing is like, why not? Of course we could do that.
A
Yeah.
B
It's just a matter of deciding. If we wanted it, we'll do it. If we don't, we won't, but that's it. And then you just see that time after time after time hanging out with them on big things, like, you know, the videos that they're going to go shoot, but the small things, and it's just a different gear. It's like, oh, your gear is like, my stick shift only goes to six, yours goes to nine.
A
Okay.
B
If I'm going to hang out with you, I now need to decide, like, how I'm going to get to eight or nine, because otherwise I'll just be sticking out. This won't be the right place for me.
A
Totally. And I think there's. I mean, I think also if you, like, experience that and you're like, you know what? I'm go with six. Totally reasonable decision. Not that arguably, maybe a better decision in some cases, like, totally fine. But there might be a 9 for any given thing. I think it's a helpful mindset.
B
You also raised a bunch of money late. So you didn't raise early on. You got to 10 million and ARR. Before you went and raised your Series A. Yep. I'm not so curious about as to why you did that, because I'm guessing the answer is pretty simple, which is like, we didn't necessarily need it. We just stayed focused on selling the product that was working. But more so when you went to go do it, what was that experience like? Cause.
A
Oh, it was.
B
You had leverage.
A
Yeah, it was great. Um, it was really funny. So people or VCs in San Francisco, broadly, like, knew we were doing well. Cause of kind of the slack channel chatter, like advantage had come up, but they sort of didn't know how well. And so there was one pitch meeting, I remember they.
B
And sorry, you kept it low key, right?
A
On purpose. Yeah, kept it low key on purpose because basically we were like, we have this great idea and everyone else thinks they can't even like spell what we're working on. Think it, you know, has KS and to do things on your feet. And I would rather they not know because then somebody's going to start knocking this off and copying. But anyway, very smart vc, very good at his job, like, go and pitch. And I start walking through the slides and I get to the ARR ramp chart the, you know, 10 at the end of it, basically, and his jaw Just drops. And he was, like, clearly speechless. And he's looking at it and he's like, I thought you were at, like, two and a half. And you're like, no, that was, you know, 10 anyway. Like, keep going. And at the end, he was sort of like, we're, like, not gonna. Like, we missed it. Like, we're not gonna be able to do this. I can, like, try to introduce you to someone else, but, like, you know, it was fine. Like, you know, there were other people, but it was this kind of interesting p. Experience. And then basically, I go into a meeting with another VC who's very good at his job, and he's like, you know what? Thought you were at 9.4. Because I'd, like, taken your Twitter chart and backed it out and taken the same, actually, and, like, counted the pixels.
B
And I was like, I did the proportions.
A
Totally.
B
She said 10. So if this is 10.
A
Yeah.
B
Where was she a year ago? 2.7 or whatever.
A
Totally. He had basically done that. And that was also. You're like, how's it? Great. So good at your job. So fun.
B
Is that who you end up going with, or. No, no, you're great, but Sequoia's calling.
A
No, but I think actually it was till the goalpost stuff, and I'm, you know, not very good at celebrating. But it was a moment where I, like, took a. I mean, a beep, like a week, and I was like, no, I am gonna, like, tell this story and what we've done, and, like, I'm deeply proud of it. And I would have told you that, but now I, like, feel overwhelmingly proud of it. Right. And, like, here's how the pieces fit together. Here's how they will fit together, and I believe it. And so that was just. Then it became like, I still kind of hate fundraising, but it was talking about something I believed in, which is fun, Right?
B
Eric told me that he thinks you're great at negotiating.
A
So funny.
B
You said that's surprising to you. Yes, but he was not. He was not wishy washy about it. He's like, she's incredible at negotiating. One of the best I've ever been around. Ask her how or why she does it. So no pressure.
A
Yeah, no, it's really surprising. I think if I'm confident in it, I'm actually confident in it. And then we'll just stand and, like, not blink, not swerve. If we're playing Chicken Won't eat the Marshmallow. It's like, I got it. Like, let me know when you want these terms. I'm happy to sit here and wait. And actually truly I'm like happy to sit there and wait at that point. So I think it's just a lot of that. It's like I won't. If I believe it, I won't flinch.
B
Cool. Well, thank you for doing this. This has been amazing. Where should people find you? Find Vanta. Maybe give it a shout.
A
Yeah. Vanta.comv a n t a dot com. If you need any help with anything security or compliance related, we would love to help you out. Awesome.
B
Well, thank you for doing this.
A
Thank you so much. I feel like I can rule the world. I know I could be what I want to. I put my all in it. Like no days off on the road, let's travel. Never looking back.
B
Hey, Sean here. Quick break. To tell you an EV Williams story. He started Twitter and before that he sold a company to Google for $100 million. And somebody asked him, they said, Ev, what's the secret, man? How do you create these huge businesses, billion dollar businesses? And he says, well, I think the answer is that you take a human desire, preferably one that's been around for thousands of years, and then you just use modern technology to take out steps. Just remove the friction that exists between people getting what they want. And that is what my partner Mercury does. They took one of the most basic needs any entrepreneur has, managing your money and being able to do your financial operations. And they've removed all the friction that has existed for decades. No more clunky interfaces. No more 10 tabs to get something done. No more having to drive to a bank, get out of your car just to send a wire transfer. They made it fast. They made it easy. You can actually just get back to running your business. You don't have to worry about the rest of it. I use it for not one, not two, but six of my companies right now. And it's used by also 200,000 other ambitious founders. So if you want to be like me, head to mercury.com, open an account in minutes. And remember, Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve bank and Trust members. Fdic. All right, back to the episode.
Podcast: My First Million
Host: Shaan Puri
Guest: Christina Cacioppo, CEO of Vanta
Release Date: November 6, 2024
The episode kicks off with Shaan Puri introducing Christina Cacioppo, highlighting her remarkable ascent from experiencing numerous failures to establishing Vanta, a company valued at $2.5 billion. Christina's candid discussion offers listeners an inside look into her resilience and strategic pivots that led to her current success.
Christina recounts her early professional endeavors, emphasizing a period marked by persistent setbacks. She admits to having "failed 22 times" before finding her footing with Vanta. This phase involved working on various projects that didn't gain traction, but each failure served as a learning experience, shaping her approach to business and product development.
Christina [00:24]: "You're putting your all into it. Like no days off on the road less traveled. Never."
A pivotal moment in Christina's career was her decision to leave a stable job at Union Square Ventures (USV) to embark on her entrepreneurial journey. Despite the secure footing provided by USV, Christina chose to "bet on the left side," a metaphor for choosing her own path over a more prestigious association.
Christina [07:20]: "I didn't like the hustle. I hustled; I just didn't enjoy the hustle of someone else's game."
This bold move was met with skepticism from peers and mentors, questioning her abandonment of the powerful USV brand. However, Christina remained steadfast, prioritizing her passion over conventional success markers.
To equip herself for entrepreneurship, Christina dedicated two years to self-education, primarily focusing on learning to code. During this period, she undertook numerous side projects—35 in total—that, despite not gaining widespread recognition, honed her technical skills and entrepreneurial mindset.
Christina [09:36]: "At the top of my site, it says, 'The function of the overwhelming majority of your artwork is simply to teach you how to make the small fraction of your artwork that soars.'"
This philosophy underscores her belief in iterative learning and the value of producing a high volume of work to achieve breakthroughs.
Christina's breakthrough came while working at Dropbox, where she identified a gap in the market for security solutions tailored to startups. Observing that existing security tools were not user-friendly for smaller companies, she conceptualized Vanta as a streamlined, accessible solution to enhance startup security efficiently.
Christina [19:19]: "The insight was wanting to start a security company that started serving startups. There seemed to be security with this huge market, but no one was really focused on startups."
This insight was pivotal, aligning her personal interests with a tangible market need, ultimately laying the foundation for Vanta's success.
Christina elaborates on Vanta's initial growth strategies, which involved aggressive outbound emailing to Y Combinator (YC) startups and leveraging word-of-mouth within founder and venture capitalist (VC) networks. These efforts were instrumental in building Vanta's early user base and establishing credibility in the competitive security landscape.
Christina [36:02]: "We tried doing everything and seeing what works. The outbound emails to YC companies were surprisingly effective."
Additionally, creative marketing tactics, such as billboards with catchy slogans, played a role in increasing brand visibility.
A significant portion of the conversation delves into the psychological challenges Christina faced during her entrepreneurial journey. From battling imposter syndrome to maintaining motivation amidst failures, Christina emphasizes the importance of mental resilience. She developed personal accountability measures, such as weekly self-surveys, to monitor her progress and manage self-doubt.
Christina [24:56]: "Figure out what makes you happy or centered, and do not give them up. For me, it was running and reading."
Her strategies highlight the necessity of maintaining personal well-being to sustain long-term entrepreneurial efforts.
Christina shares her fundraising journey, detailing both unsuccessful and successful pitches to venture capitalists. Initially, she encountered resistance due to misconceptions about Vanta's progress. However, by clearly presenting her company's traction and growth metrics, she eventually secured funding from savvy investors who recognized Vanta's potential.
Christina [46:16]: "I start walking through the slides and get to the ARR ramp chart... his jaw just drops. He was clearly speechless."
This anecdote underscores the critical importance of demonstrating tangible progress and market validation when seeking investment.
The discussion transitions to Christina's approach to validating startup ideas. She advocates for engaging directly with potential customers to understand their problems deeply before developing solutions. This method minimizes the risk of building products that do not meet market needs.
Christina [33:03]: "The hard part is, does anyone want my thing at the end? How much of the validation can you front load there?"
She references "The Mom Test," emphasizing the need for objective, problem-focused conversations to gather honest feedback and avoid biased positives.
Christina challenges conventional wisdom by suggesting that consistency might sometimes be overrated. Instead, she believes in dynamic progression, where goals evolve as the company grows. This perspective promotes adaptability and continuous improvement rather than rigid adherence to initial plans.
Christina [38:18]: "Consistency is actually underrated. I think Vanta's taught me consistency is actually underrated."
This insight encourages entrepreneurs to remain flexible and responsive to changing circumstances, fostering a culture of innovation.
Towards the end of the episode, Shaan commends Christina's exceptional negotiation skills, describing her as "incredible at negotiating." Christina attributes her prowess to unwavering confidence in her vision and the ability to stand firm during negotiations.
Christina [48:57]: "If I believe it, I won't flinch. If we're playing Chicken, I won't eat the marshmallow."
Her leadership style underscores the importance of conviction and resilience in navigating business challenges.
The episode concludes with Christina reflecting on her journey, celebrating Vanta's achievements, and encouraging aspiring entrepreneurs to "bet on themselves." Her story is a testament to the power of perseverance, strategic learning, and maintaining a clear vision despite numerous setbacks.
Christina [49:03]: "If you need any help with anything security or compliance related, we would love to help you out."
Embrace Failure: Christina's 22 failures were stepping stones to her success with Vanta, highlighting the value of persistence.
Self-Education: Investing time in learning and skill-building was crucial for Christina's entrepreneurial journey.
Customer-Centric Validation: Engaging with potential customers can effectively validate business ideas and ensure market fit.
Mental Resilience: Maintaining personal well-being and managing self-doubt are essential for sustained entrepreneurial effort.
Adaptive Goal Setting: Flexibility in goals allows businesses to navigate growth and changing market dynamics effectively.
Negotiation Confidence: Strong negotiation skills stem from unwavering belief in one's vision and the ability to stand firm under pressure.
Christina [10:06]: "The function of the overwhelming majority of your artwork is simply to teach you how to make the small fraction of your artwork that soars."
Christina [24:56]: "Figure out what makes you happy or centered, and do not give them up."
Christina [33:03]: "The hard part is, does anyone want my thing at the end?"
Christina [38:18]: "Consistency is actually underrated."
Christina [48:57]: "If I believe it, I won't flinch."
This episode of My First Million offers a comprehensive exploration of Christina Cacioppo's entrepreneurial journey, providing valuable lessons on resilience, strategic learning, customer validation, and leadership. Her insights serve as a guiding framework for aspiring entrepreneurs aiming to navigate the complex landscape of building a successful startup.