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

Episode 646: Shaan Puri ( https://x.com/ShaanVP ) talks to Vanta founder Christina Cacioppo ( https://x.com/christinacaci ) about quitting her job and betting on herself. — Show Notes: (0:00) Stumblehustling into USV (4:36) Betting on the left side of your email address (8:30) The art of fear (11:47) Making bad art (13:30) The marshmallow test (17:26) Startup advice to beware of (18:16) The idea for Vanta (21:00) The only question that matters (22:30) Managing your mind (27:47) How to pick an idea to chase (29:03) The real origin of Vanta (31:00) Building a flywheel (36:06) Controversial opinions (40:49) Pushing past the no (46:17) Not flinching during negotiations — Links: • Vanta - https://www.vanta.com/ — Check Out Shaan's Stuff: Need to hire? You should use the same service Shaan uses to hire developers, designers, & Virtual Assistants → it’s called Shepherd (tell ‘em Shaan sent you): https://bit.ly/SupportShepherd — Check Out Sam's Stuff: • Hampton - https://www.joinhampton.com/ • Ideation Bootcamp - https://www.ideationbootcamp.co/ • Copy That - https://copythat.com • Hampton Wealth Survey - https://joinhampton.com/wealth • Sam’s List - http://samslist.co/ My First Million is a HubSpot Original Podcast // Brought to you by The HubSpot Podcast Network // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  And at the time, my email was [email protected]. 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?

• 0:09Shaan Puri?

  You're betting on the left side.

• 0:10Speaker 00

  You're betting on the left side. And like, why would you do that? And like, what do you think will happen here?

• 0:24Shaan Puri?

  I don't know if you know this fun fact. Do you know what you, Katy Perry, and Serena Williams have in common?

• 0:29Speaker 00

  I've got nothing.

• 0:31Shaan Puri?

  You're all on Forbes self-made women list.

• 0:33Speaker 00

  I hate that list. I hate that list.

• 0:34Shaan Puri?

  And you are ahead of them. Isn't that kind of amazing?

• 0:37Speaker 00

  I would have preferred that list never existed. Yes.

• 0:39Shaan Puri?

  You have that Midwest modesty.

• 0:41Speaker 00

  Yes. You're like, nothing good will come from that list.

• 0:43Shaan Puri?

  Yeah, yeah. Those lists are, they are sort of made for the wrong type of people.

• 0:48Speaker 00

  Yes. Or jail time later, or something. Whatever the last that. It was never on 30 under 30, and I'm deeply glad about that now.

• 0:55Shaan Puri?

  Yeah, that turned out to be an anti-signal. You know, 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.

• 1:39Shaan Puri?

  And it's not like it hit right away, and you created Vanta, and you created this, you know, 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.

• 2:00Speaker 00

  Yeah.

• 2:01Shaan Puri?

  You have the job at USV. Which I think you kind of hustled your way into.

• 2:05Speaker 00

  I would say stumble hustled.

• 2:07Shaan Puri?

  Okay.

• 2:07Speaker 00

  They didn't like 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 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.

• 2:34Shaan Puri?

  What kind of links?

• 2:36Speaker 00

  It was Twitter, Flickr, through the era of this. And I had started a design blog a couple of months before and I lived in Berlin because I wanted to be like a designer who lives in Berlin and those people seemed to have design blogs. So I started one and that was it. And they hired me, which is crazy.

• 2:59Shaan Puri?

  And I read something that was like they, maybe Fred or somebody at the USB team was telling you, "You should specialize in crypto. You should become a crypto VC." Is that true?

• 3:08Speaker 00

  Kind of. It was actually when 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, ew, but I don't think I like it. And again, what's going on? And one of my hangups 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 at 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 100 out of 100 times.

• 3:44Shaan Puri?

  Which is what's a maybe a partially imposter syndrome, but also maybe hyper logical.

• 3:49Speaker 00

  Yeah, I think like, yeah, but like also true. Anyway, and I basically said that to Fred and he said two things, which, or he said a couple of things, so deeply insightful. One was like, well, you know, one, you've got to like get over that. And you can either get over that by sort of out hustling people and like kind of the figure till you make a 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.

• 4:27Shaan Puri?

  Right.

• 4:27Speaker 00

  I didn't take it, but like.

• 4:28Shaan Puri?

  Because you didn't believe in crypto, or you were just like, that's not me?

• 4:31Speaker 00

  I'm just like, I don't know if I want to be an investor.

• 4:33Shaan Puri?

  Okay.

• 4:34Speaker 00

  Even though it's great and it's wonderful and it has all these great attributes and like, everyone else wants to be VC, but like, I want to go make things.

• 4:40Shaan Puri?

  So you decided to go make things. Take me back to that decision. Was that easy?

• 4:44Speaker 00

  No, I was so anxious.

• 4:45Shaan Puri?

  Was everybody patting on the back and saying, you're gonna make this happen?

• 4:48Speaker 00

  Definitely not. What I did and what my plan was, was I'd saved my bonus from the prior year and it's kind of like a finance bonus. And I was gonna live off of that as long as I could. So like, no job, but a bunch of structure, learn to code, learn 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. Cause 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, investors, like, I can't stop.

• 5:25Speaker 00

  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? Cause clearly you, you don't know what you want to do. And then some amount of, like, kind of the tougher stuff, I think, where a couple, 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, my email was [email protected]. And it was like, the right side, that usv.com is way more powerful than the left side.

• 6:10Speaker 00

  And now you're giving that up. And so what are you?

• 6:13Shaan Puri?

  You're betting on the left side.

• 6:14Speaker 00

  You're betting on the left side. And like, why would you do that? And like, what do you think will happen here?

• 6:18Shaan Puri?

  So you have the good job.

• 6:19Speaker 00

  Yep.

• 6:20Shaan Puri?

  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. 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.

• 6:42Speaker 00

  On purpose.

• 6:43Shaan Puri?

  I built all these things.

• 6:44Speaker 00

  Yeah, none of which you've heard of.

• 6:46Shaan Puri?

  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.

• 6:58Speaker 00

  Yep.

• 6:58Shaan Puri?

  It may not have felt that way at the time, but.

• 7:00Speaker 00

  It like, I kinda knew I was supposed to feel that way. And then day to day, there was some amount of like, I spent more than my like daily cash allowance, you know? But like, I kinda 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 it 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 USV office. And so I got up every day and I got trips 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 did their stuff.

• 7:41Shaan Puri?

  By the way, because I feel like there's psychologically something to actually dressing up like you're going somewhere.

• 7:46Speaker 00

  Yeah, I mean, tech dress up. But it was like, I did not wear pajamas.

• 7:48Shaan Puri?

  Right, right.

• 7:49Speaker 00

  Like, um, 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, you know, JavaScript to varying degrees. And then like go home at, you know, 6:00 PM or 7:00 PM 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 nine, 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? And why are you tan? And I'm being like, I'll complain for this. You know, like, I'll withdraw. Everything is PTO to me. But he was like, also like, oh, yeah, I got this.

• 8:33Speaker 00

  Like, that's, that was kind of like a fun, fun moment, too.

• 8:36Shaan Puri?

  Yeah, I like that. So you have this era, which is kind of like in the movies, it's the montage. It's, 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, can you explain that?

• 9:06Speaker 00

  Yeah, I think it's deeply true of creative projects. And I think startups or businesses or, you know, internet art is like, they're all creative projects. One thing I learned at USP, 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 USP, I was like, everyone is Mark Zuckerberg. Not actually, but like, everyone, you know, like startup founders are people who have an idea.

• 9:33Shaan Puri?

  Visionary.

• 9:34Speaker 00

  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, I'm kind of like, oh, shoot, I'm like, not, it's never worked for me, so I'm probably not one of them. And USP was just so helpful in just abusing 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 five, and it might be thing 55. But no one really talks about that. Because it's both because it's painful and kind of not fun. You know, it's supposed to be romantic, but actually it just kind of sucked.

• 10:18Speaker 00

  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.

• 10:36Shaan Puri?

  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.

• 10:40Speaker 00

  Yeah.

• 10:40Shaan Puri?

  I will bump into a stranger. Our papers will fall on the floor.

• 10:43Speaker 00

  We'll swap a paper.

• 10:44Shaan Puri?

  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.

• 10:51Speaker 00

  Yeah.

• 10:51Shaan Puri?

  You'll almost count yourself out of other things that could have worked otherwise.

• 10:55Speaker 00

  It's like very that.

• 10:55Shaan Puri?

  You know, if you watch The Social Network, you're like, that's just how it is. Brilliant genius, 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.

• 11:18Speaker 00

  Right.

• 11:18Shaan Puri?

  Let's just make some bad art today.

• 11:19Speaker 00

  Yeah.

• 11:20Shaan Puri?

  And the analogy I gave, and 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.

• 11:30Speaker 00

  Yep.

• 11:31Shaan Puri?

  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.

• 11:37Speaker 00

  Right.

• 11:37Shaan Puri?

  Leaf. 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.

• 11:56Speaker 00

  Do you know the story about making pots?

• 11:58Shaan Puri?

  No.

• 11:58Speaker 00

  From the same book. So, and I think it was like around the chapter 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 pot. And student one spends all semester crafting the perfect pot.

• 12:27Speaker 00

  And hands it in at the end. And student two makes two pots a day. And they're all back for a long time. Right. But over the course of semester, hands in whatever, like 300 pots. And like, who gets a better grade?

• 12:39Shaan Puri?

  Of course.

• 12:39Speaker 00

  They're 300, right? Yeah, yeah. But it's like that concept. It's like so true.

• 12:43Shaan Puri?

  And you have to live it almost to really internalize it.

• 12:45Speaker 00

  Yeah.

• 12:45Shaan Puri?

  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.

• 13:27Shaan Puri?

  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 because you didn't like, you like backloaded the possible failure, you know, the failure mode or the sort of test of the, of the idea. You spend all your time kind of planning and architecting this brilliant, beautiful thing. And the, 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.

• 14:11Shaan Puri?

  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.

• 14:19Speaker 00

  Yep.

• 14:19Shaan Puri?

  And that sort of iterative thing about testing the riskiest assumption.

• 14:22Speaker 00

  Yep.

• 14:23Shaan Puri?

  Is, is maybe important. It seems like for you, did you make that mistake of kind of like over analyzing, over planning at the beginning, but like not testing with customers?

• 14:32Speaker 00

  Less than very beginning, because at the beginning I was just, 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. Um, 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 gonna be 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, this is a 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 wanna see what's on their bookshelf?

• 15:16Speaker 00

  Anyway, so I was like, okay, what if I can get everybody's books online? But it was like, clearly, this is not a business. Like, best case, I'm making like 50 bucks a month, you know, Amazon referrals. It's like, not a business.

• 15:26Shaan Puri?

  But you did it anyways, why?

• 15:27Speaker 00

  Cause I wanted it. I want, and it was a good, it wasn't, you know, like, you do your initial coding tutorials and you're like, or making whatever the other person wants to make, which is not what you wanna make. And like, I actually wanted this thing. And it like forced me to be like, oh, you know, now I want like an animation when you shelve the books. So you, right? And then you'd like learn about CSS animations, whatever it is.

• 15:51Shaan Puri?

  And so you, so you started building stuff for yourself?

• 15:53Speaker 00

  Yep.

• 15:53Shaan Puri?

  Did you ever switch gears to, okay, now, now I'm gonna do the startup startup. I'm gonna do the thing that might actually, you know, get me out of poverty, like self-induced poverty, basically.

• 16:03Speaker 00

  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 like hold everything in our heads and you have to teach yourself to think like a computer and like read through code, which is like not how a person, you know, think like a computer. And once you have that, everything gets easier, but like, why? We are typing on computers. And so I kind of got on this, like, if we could make our programming environments better, you can like more, they will just make more sense and more people will like learn to code. And so, you know, I was really into that personal problem, also the like, you know, live in the future and build back, you know, whatever, all the, all the startup trope advice.

• 16:47Shaan Puri?

  I'm curious about that. What startup trope advice actually helped you?

• 16:49Speaker 00

  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? Um, and so.

• 17:10Speaker 00

  My version of that is like, look, if there is something personally meaningful, like by all means, go for it.

• 17:15Shaan Puri?

  That's top ranked.

• 17:16Speaker 00

  Totally. But like, second best is like, find someone else with the problem and deeply, deeply understand them. I think there's a very, 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.

• 17:36Shaan Puri?

  Right.

• 17:37Speaker 00

  But I can tell you a story about Vanta where Vanta fits that.

• 17:39Shaan Puri?

  Yeah.

• 17:40Speaker 00

  And it does, but it's.

• 17:41Shaan Puri?

  But that's in retrospect. Yeah.

• 17:42Speaker 00

  Yeah.

• 17:42Shaan Puri?

  So what was the actual in the moment way that you stumbled into this idea of Vanta that now seems obvious as all great ideas do, once they exist. And now there's you guys and 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.

• 17:59Speaker 00

  Yep.

• 17:59Shaan Puri?

  What was the insight for that?

• 18:01Speaker 00

  The insight was wanted to start a security company that started serving startups. There seemed to be like, security was this huge market, but no one was really focused on startups and startups didn't use security tools. And I'm sort of like, why? And like, when does this become a 90 quadrillion, like go from a zero TAM to like 90 quadrillion dollar market size in precise terms?

• 18:20Shaan Puri?

  Yeah, that's the official number.

• 18:21Speaker 00

  Yeah, exactly.

• 18:23Shaan Puri?

  But wait, why security? Cause 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?

• 18:36Speaker 00

  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.

• 18:44Shaan Puri?

  Right.

• 18:44Speaker 00

  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, you know, 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, you know, 18 months of my life learning about security on the internet,

• 19:29Speaker 00

  could have been worse.

• 19:30Shaan Puri?

  Yeah.

• 19:30Speaker 00

  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.

• 19:36Shaan Puri?

  Well, connect the dots for me. So you, you took the year or multiple years off to teach yourself two years?

• 19:42Speaker 00

  Yeah.

• 19:42Shaan Puri?

  But then you go to Dropbox.

• 19:43Speaker 00

  Yeah.

• 19:44Shaan Puri?

  So you go back to getting a job.

• 19:45Speaker 00

  Yeah.

• 19:46Shaan Puri?

  So I feel like we, like, there's a part of the story that's like, I iterated, iterated, finally I found it. No, no, no. Finally, you found a job at Dropbox.

• 19:52Speaker 00

  Yeah, because 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, never worked with people. Also, my, my like friends are kind of getting promoted and like, I can, you know, like, it's unclear if I'm employable. Like, this seems bad. And I was really frustrated because again, I like, I wouldn't tell people I wanted a startup to come out of that. But like, I did. But I also at the time was like, well, nothing I've worked on should be a startup. Right?

• 20:20Shaan Puri?

  So what was that story you told yourself? So you, you spent the two years, you bet on yourself.

• 20:25Speaker 00

  Yep.

• 20:26Shaan Puri?

  Which sounds amazing. That's a great T-shirt, bet on yourself.

• 20:28Speaker 00

  Yeah.

• 20:29Shaan Puri?

  But the reality of it, I do it for, I told you, I did it for eight years.

• 20:31Speaker 00

  Yeah.

• 20:32Shaan Puri?

  And I was delusional enough to keep going.

• 20:34Speaker 00

  Yeah.

• 20:35Shaan Puri?

  But also objectively, it was bad and I should have, I had to tell myself certain stories in order to either, A, keep going or to like, just maintain a self, a sense of confidence.

• 20:46Speaker 00

  Yeah.

• 20:47Shaan Puri?

  Beyond that, because the evidence was telling me you suck.

• 20:49Speaker 00

  Yeah, yeah, yeah.

• 20:50Shaan Puri?

  And I just couldn't tell myself you suck because then I definitely suck.

• 20:52Speaker 00

  Yeah.

• 20:53Shaan Puri?

  What were you saying when the evidence kind of said, you suck?

• 20:57Speaker 00

  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?

• 21:10Shaan Puri?

  You made that for yourself.

• 21:11Speaker 00

  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's 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.

• 21:47Shaan Puri?

  And so that's how you were stopping those projects?

• 21:48Speaker 00

  Yeah.

• 21:49Shaan Puri?

  You, when we, I sent you some questions ahead of this to try to understand what, what you think is important to talk about, what 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.

• 22:05Speaker 00

  Yep.

• 22:06Shaan Puri?

  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?

• 22:11Speaker 00

  It's, I think, hard, hard to do, hard to teach. I think what I try to tell people is figure out what, like, it's, it's personal and not personal sensitive, but like, personal, like, specific to you. And figure out what makes you happy or centered, whatever those things are, and like, do not give them up. And so for me, for years, it was like, you know, running three or four times a week. And like, exercise, sure, but it was actually just like the mind clearing catharsis, kind of meditative, like, running. And, you know, it's like, running for me, but like, whatever for someone else. And it's like, whatever that thing is, do not give it up.

• 22:54Speaker 00

  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.

• 23:02Shaan Puri?

  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?

• 23:07Speaker 00

  It's just like that feeling where you're 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?

• 23:17Shaan Puri?

  So for you, running is one. What else?

• 23:18Speaker 00

  Running was one. Reading? Like, not in any... I mean, kind of an elegant analogy, 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.

• 23:32Shaan Puri?

  Right.

• 23:33Speaker 00

  And so there's a part of that that just feels like me.

• 23:36Shaan Puri?

  Yeah, because I was looking, you read like, I don't know, 30, 50 books a year or something.

• 23:39Speaker 00

  Yeah, but it's like, I mean, yes, I want to learn things and like blah, blah, blah. But actually, it's just like, it is centering.

• 23:45Shaan Puri?

  How do you do that? When I was running a company, and by the way, mine was not a 2.4 or 5 billion dollar 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 as simple as that?

• 23:58Speaker 00

  Yeah, like actually.

• 24:00Shaan Puri?

  Eric told me that you are like extremely quick with reading. He's like, she would take a bus to work.

• 24:06Speaker 00

  Yeah, and read the book.

• 24:07Shaan Puri?

  And read the whole book on the bus ride.

• 24:09Speaker 00

  Yeah, I mean, over the course of a week or so, but yeah, like, actually, Tuesday.

• 24:12Shaan Puri?

  The way he said it was more legendary. He was like, to and from, cover to cover.

• 24:16Speaker 00

  No, I wasn't it.

• 24:18Shaan Puri?

  You should roll with that.

• 24:19Speaker 00

  I actually still take a bus to work, part of it, so I can just sit there and like.

• 24:23Shaan Puri?

  You bus to work?

• 24:24Speaker 00

  Yeah. Because look, if I take a car, I'm just gonna like sit in the back with my laptop, writing emails, you know, and in a bus, like, oh, San Francisco bus, I'm not putting on my laptop on that, unless something's like really gone wrong. And so it just forces me to like, sit there and have 20 minutes between home and work. And I like that much more.

• 24:43Shaan Puri?

  It's almost like, you know how people are like obsessed with cold plunges?

• 24:44Speaker 00

  Yes.

• 24:45Shaan Puri?

  I think the more hardcore version is take a San Francisco bus to work. It's like, wow, you can endure an 18 minute bus ride with like.

• 24:51Speaker 00

  The buses aren't bad. 5R used to be my bus. 5R is a great.

• 24:55Shaan Puri?

  I used to take the 38 and the 38 is like an actual zoo. It's like, anything can happen.

• 25:00Speaker 00

  Yeah, yeah, yeah. No, 5R, great bus. I miss it. I miss it.

• 25:04Shaan Puri?

  Okay, so, so Ben, your own psychology, you said, figure out what makes you feel like you, most of you, and make sure you stick with those things, keep doing those things. It'll kind of keep you centered with it. What about Ben's 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?

• 25:28Speaker 00

  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, the bat nut, like, my worst-case outcome was becoming a product manager at Dropbox. The height of Dropbox's power. Like, my life was great.

• 25:42Shaan Puri?

  Did you just say the bat nut?

• 25:43Speaker 00

  Yeah, right? But like, my life was great. It did not feel great at the time. It was totally great. And again, I knew I was like 5% aware of that, 10%, but that was not the lived feeling.

• 25:52Shaan Puri?

  Do you use negotiation terms like that just regularly?

• 25:55Speaker 00

  Hopefully not. That sounds kind of obnoxious. I'll try not to now.

• 25:58Shaan Puri?

  No, I like that.

• 26:00Shaan Puri?

  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.

• 26:08Speaker 00

  Yeah.

• 26:08Shaan Puri?

  It just gives you, like, actually, like, 2X the valuation. It just creates this extra aura.

• 26:13Speaker 00

  Totally true.

• 26:13Shaan Puri?

  Wow, she's, she's barefoot all the time? Why? Oh, interesting. She must be one of those real outlier types.

• 26:18Speaker 00

  Oh, my gosh.

• 26:20Shaan Puri?

  All right. Well, I asked you about this list of ideas that you did. So I've looked back at 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?

• 26:41Speaker 00

  Like, there are projects, and I say that with deep love, but like, they're not businesses.

• 26:47Shaan Puri?

  The voice assistant for biologists. Yeah, that doesn't sound like a great business.

• 26:50Speaker 00

  That was, 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

• 27:05Shaan Puri?

  Learned your lesson.

• 27:06Speaker 00

  so many times.

• 27:08Shaan Puri?

  What about now? So if you, 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?

• 27:33Speaker 00

  Yeah, I think just so much of what I think about that's not kind of directly in Vanta'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-wigged them together in this Rube Goldberg machine, and the marbles are all up on the floor, and like... If anyone wants to be to be SaaS, just like fix that, go full stack on all that. But for people who don't want to be to be SaaS, which there are hopefully many. I think the process of Vanta came out of, I mean, I of course, I mean, I liked it going in, but of course I really like it, but that was pick something you want to learn about and just go

• 28:15Speaker 00

  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 the space.

• 28:24Shaan Puri?

  The story I heard about Vanta, which sometimes we make up these retrospect stories. So I don't know, you tell, you can.

• 28:30Speaker 00

  I tried to actually tell the, the true one.

• 28:32Shaan Puri?

  Like blink twice if it's true.

• 28:33Speaker 00

  Yeah.

• 28:34Shaan Puri?

  But it was, you're at Dropbox, you work on this thing called paper, which was this, I remember like seeing paper at the time. It was like this idea of this collaboration tool.

• 28:41Speaker 00

  Dropbox is version of Google Docs.

• 28:43Shaan Puri?

  Yeah, Dropbox is Google Docs. You go to launch it and it's like, hey, we don't have stock two, so can't really launch or customers can't use it. And you were like, stock what?

• 28:51Speaker 00

  Yep.

• 28:52Shaan Puri?

  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.

• 29:03Speaker 00

  Yep.

• 29:03Shaan Puri?

  Dropbox had a security team that was going to be able to try to solve those problems, but like the average startup doesn't.

• 29:09Speaker 00

  Yep.

• 29:09Shaan Puri?

  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.

• 29:24Speaker 00

  Yep.

• 29:24Shaan Puri?

  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?

• 29:35Speaker 00

  All true.

• 29:39Speaker 00

  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. They just sounded awful, especially when we were trying to launch and even figure out if we had product market fit. So the idea of like, we're going to go two years of work to then see if we have product more 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 sort of five things on the list. Like, kind of the point where you're like, okay, I can write, you know, maybe someone's shoddy job. 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?

• 30:21Speaker 00

  And so like, how much of the validation can you front load there?

• 30:25Shaan Puri?

  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.

• 30:32Speaker 00

  Yep.

• 30:32Shaan Puri?

  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?

• 30:40Speaker 00

  Yeah.

• 30:40Shaan Puri?

  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.

• 30:50Speaker 00

  Yeah. So on the false positives, anything that is not, can you do this for me now, tomorrow, next week? Is a no. And people are really kind, and they want to be kind. And so they don't say, like, rarely do they say no. But a lot of like, oh, maybe next quarter. Like, I don't need this, but my friend might, hard no.

• 31:08Shaan Puri?

  Yeah, you should date my friend.

• 31:09Speaker 00

  Hard no. Totally. Hard no.

• 31:13Speaker 00

  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 that's what ended up being coworkers, former coworkers. Because you had like, some like, well, I don't know if you know anything about this topic, but you're kind of a nice-ish person. And so I'll like, give you a half an hour sort of thing. And then just fan out from there. At the end, when they're like, well, you know, you ask them, do you have anybody else? And they 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.

• 31:43Shaan Puri?

  Yeah, I think that's an important one. Make it easy for them.

• 31:45Speaker 00

  Yes.

• 31:45Shaan Puri?

  To do the thing they said they want to do.

• 31:47Speaker 00

  Oh, yeah. Like, follow up and be like, thanks so much for meeting me. Like, I would love to talk to your friend, Eric, who said this. Like, here's what I'm working on. Like, and just like, assume they will, like, write them an email they will forward.

• 31:56Shaan Puri?

  Exactly. So you, have you ever read this thing called the mom test?

• 32:01Speaker 00

  Yes.

• 32:02Shaan Puri?

  Do you subscribe to that?

• 32:03Speaker 00

  Yeah, generally.

• 32:04Shaan Puri?

  Yeah, they, that was helpful to me when it was, there's only, I don't even actually remember what was in the book. Only one line, which was, they can't tell you about the solution, but they can tell you about their problem. 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.

• 32:23Speaker 00

  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 gonna like-

• 32:38Shaan Puri?

  Don't break rapport.

• 32:39Speaker 00

  Exactly, exactly. Like a lot of that-

• 32:40Shaan Puri?

  Yeah, that's true. I think I do that. And it sort of is like a problem because it's kind of a know it all move.

• 32:46Speaker 00

  Right.

• 32:47Shaan Puri?

  And then it makes them feel like their mind goes over there.

• 32:49Speaker 00

  Exactly.

• 32:50Shaan Puri?

  Oh, am I being stupid? Did I say something stupid?

• 32:51Speaker 00

  Exactly. Where you just like want them to like stream of consciousness at you, basically.

• 32:56Shaan Puri?

  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.

• 33:05Speaker 00

  Yeah.

• 33:05Shaan Puri?

  And I've seen your like ARR chart, which looks like a beautiful hockey stick.

• 33:09Speaker 00

  Yeah, totally.

• 33:10Shaan Puri?

  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 felt was interesting, unique, that kind of took hustle or creativity?

• 33:24Speaker 00

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

• 33:50Shaan Puri?

  So you emailed a bunch of Y C people, backed out the ball rolling. What happened after that?

• 33:54Speaker 00

  Honestly, the early strategy was like just do and try everything and then see what works.

• 34:01Shaan Puri?

  So what did work?

• 34:02Speaker 00

  The outbound worked. There was a word of mouth. We tried actually really hard in the early days to basically build this call response in like founder Slack channels or V C Slack channels where someone said SOC 2 and someone else would say Vanta. And you just wanted this, you know-

• 34:16Shaan Puri?

  And how do you do that? You're saying like build the brand in people's minds?

• 34:19Speaker 00

  Yeah. And that was great for a while. And then a bunch of knockoffs came and there was a bunch of other ways to get SOC 2. And so that, that association-

• 34:30Shaan Puri?

  I remember you guys had the billboard. It was like- But is it compliance that doesn't suck too much?

• 34:34Speaker 00

  Yeah, still up.

• 34:35Shaan Puri?

  Yeah, that was good.

• 34:36Speaker 00

  Still up.

• 34:39Speaker 00

  Yeah, I joke with people like we make software, but like we also make a billboard and we're equally known for both.

• 34:46Speaker 00

  Equally as important.

• 34:50Speaker 00

  What else? Uh, 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.

• 35:02Shaan Puri?

  And that's what happened. Somebody on your team pitches you this?

• 35:05Speaker 00

  Eric was like, I want 20K to go on Twit, This Week in Startups or something. And I like rolled my eyes and said, fine, whatever, go. It totally worked. She was totally right.

• 35:16Shaan Puri?

  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.

• 35:26Speaker 00

  No.

• 35:27Shaan Puri?

  All right. Well, I'll ask you about a couple 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.

• 35:40Speaker 00

  Oh, yeah. People feed a lot into this. I'm just like joking with myself because I say, contact me through these four ways that are all have totally different names on them. So like this is like minor.

• 35:50Shaan Puri?

  Naming consistency is overrated.

• 35:51Speaker 00

  Yeah, it's just like minor self-awareness thing that I think people think is meant to be a broad philosophical statement. Do I actually think it's a broad philosophical statement? No, probably not. I think Vanta taught me consistency is actually underrated.

• 36:04Shaan Puri?

  Yeah, I was gonna say, you strike me as somebody who's consistency first.

• 36:07Speaker 00

  Yeah.

• 36:09Shaan Puri?

  It's bad, it's bad when the goalposts move. I don't know if you're saying you think this or that other people think this.

• 36:13Speaker 00

  I think other people, the advice tends to be right. Like, you know, if your goalposts keep moving, it's hard to find happiness. And like, you're always finding happiness.

• 36:20Shaan Puri?

  Explain what it means. So like, what does that even mean?

• 36:21Speaker 00

  Yeah, like, uh, I think, I mean, it's about in lots of forms of life, but like, let's take startup founders, just because they're right. It's like, you want to start a company, you want to hire some people, you want to write the seed round, you want to get to like a million in ARR. But then by the time you get there, you're like, actually, I want to get to 10, right?

• 36:36Shaan Puri?

  Right, that's it, yeah.

• 36:37Speaker 00

  Yeah, that's it. 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...

• 37:02Speaker 00

  Slash downside is if you're like only happy when you hit a goalpost and then you're moving them, like you'll never be happy. If you actually just like the work.

• 37:10Shaan Puri?

  Right.

• 37:11Speaker 00

  So 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.

• 37:18Shaan Puri?

  My formula is progress equals happiness, which is that no matter where you are, 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.

• 37:33Speaker 00

  Yeah.

• 37:33Shaan Puri?

  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.

• 37:39Speaker 00

  Right, right.

• 37:39Shaan Puri?

  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.

• 37:46Speaker 00

  Yep.

• 37:47Shaan Puri?

  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. Why would I stop my progress? That stops my happiness.

• 37:56Speaker 00

  Yeah.

• 37:57Shaan Puri?

  It's a different way of looking at it.

• 37:58Speaker 00

  Do you remember, deep cut, 10, 12 years ago, Jess, who's the founder of Polyvor at the time now, Sequoia, wrote a blog post about founder psychology?

• 38:07Shaan Puri?

  No, what did it say?

• 38:08Speaker 00

  It was like, 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.

• 38:31Shaan Puri?

  Right.

• 38:31Speaker 00

  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.

• 38:41Shaan Puri?

  Yeah, it's the peak to trough that you feel. You don't really even recognize that you've gotten higher progressively each time. You also have another one, which is high standards are bad. You think that in generally, you said people don't say this, but they imply it in different ways that don't have such high standards.

• 38:56Speaker 00

  Right.

• 38:57Shaan Puri?

  What is, what's a situation where that's come up for you or you felt that?

• 39:00Speaker 00

  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 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.

• 39:28Speaker 00

  Everywhere by accident, it's not to say I had, I mean, probably hopefully had 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?

• 39:41Shaan Puri?

  What's an example of that? Where would somebody feel that?

• 39:44Speaker 00

  A couple of places, but I guess in go to market are expectations around quota, around attainment on that. They're way off industry. They're way higher. And I think if you just, if one just hears them in a vacuum, they're sort of like, what is what? Like, why would I, why would I sign up for that? Then they join and it's like, oh, because you're surrounded by people who are like into what they do, getting better every day, want to get better every day, care a lot. And that sort of environment can be like really infectious.

• 40:12Shaan Puri?

  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?

• 40:19Speaker 00

  I know.

• 40:20Shaan Puri?

  You know who Mr. Beast is?

• 40:21Speaker 00

  Yeah, yeah.

• 40:22Shaan Puri?

  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, 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 done, like, the number one thing, you go hang out with Jimmy for a couple of days. Like, you walk away and you're like, oh, he, that's what people, that's what it means when people say reality. You know, Steve Jobs used to have this reality distortion field.

• 40:52Speaker 00

  Yep.

• 40:53Shaan Puri?

  And it's, and literally, he, his company's 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, 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. Hey, like, that can't be the end of the story. And we saw it on every little thing. Like, for example, we wanted to play basketball the next day and it was midnight. And somebody was like, oh, man, I can't wait till tomorrow. Like, I just want to play. And he goes, well, why do we have to wait?

• 41:38Shaan Puri?

  Like, well, it's midnight. Jimmy, what are you gonna do? He's like, I'm sure there's a gym around here somewhere. Let's go, let's go find one. And we're like, yeah, but they're gonna be locked. It's midnight, like, schools aren't gonna be open. He's like, call the athletic director. So 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 1,000 bucks. See if they'll come open it. And like, part of it was like, oh, he just throws money at every problem. But actually, it's not about throwing money at it.

• 42:00Speaker 00

  Yeah.

• 42:01Shaan Puri?

  Everybody else would immediately just default to like, this is not possible, not feasible, not, not gonna be doable. Whereas his default assumption on any, any given thing is like, why not? Of course we could do that.

• 42:10Speaker 00

  Yep.

• 42:11Shaan Puri?

  It's just a matter of deciding. If we wanted it, we'll do it. If we don't, we won't. But that's it. And you just see that time after time after time, hanging out with them on big things, like, you know, the videos that they're gonna go shoot. But the small things, and it's just a different gear. It's like, oh, your gear is like, my, my stick shift only goes to six, yours goes to nine.

• 42:26Speaker 00

  Right.

• 42:27Shaan Puri?

  If I'm gonna hang out with you, I now need to decide like, how I'm gonna get to eight or nine.

• 42:30Speaker 00

  Yep.

• 42:31Shaan Puri?

  Because otherwise, I'll just be sticking out. This won't be the right place for me.

• 42:34Speaker 00

  Yep. Yeah, totally. And I think there's a, I mean, I think also, if you like, experience that and you're like, you know what? I'm go with six.

• 42:42Shaan Puri?

  Right.

• 42:42Speaker 00

  Totally reasonable decision. Like, not that, you know, arguably maybe a better decision in some cases. It's like, totally fine. But the, the like, there might be, there might be a nine for any given thing. I think it's a helpful mindset.

• 42:56Shaan Puri?

  You also raised a bunch of money late, so you didn't raise early on. You got to 10 million in ARR before you went and raised your Series A.

• 43:05Speaker 00

  Yep.

• 43:06Shaan Puri?

  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?

• 43:19Speaker 00

  Oh, it was really fun. Yeah, it was great. It was really funny. So people, or VCs in San Francisco broadly, like, knew we were doing well, because of kind of the Slack channel chatter, like, advanced had come up. But they sort of didn't know how well. And so there was one pitch meeting, I remember they-

• 43:36Shaan Puri?

  And sorry, you kept it low-key, right?

• 43:38Speaker 00

  Yeah, kept it low-key on purpose. Because basically, we were like, we have this great idea and everyone else thinks they can't even like, spell what we're working on. Think it, you know, has K's and to do it things on your feet. And I would rather they not know because then somebody's going to start knocking soft 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, the 10. And anyway, it's like, keep going. And at the end, he was sort of like, we're like, not going to, like,

• 44:21Speaker 00

  we missed it. Like, we're not going to be able to do this. I can like, try to introduce you to someone else. But like, you know, there was, like, you know, there were other people. But it was this kind of interesting pitch experience. And then, basically, I go into a meeting with another VC who's very good at his job. And he's like, you know what? Thought you were at 9.4. Because I'd like, taken your Twitter chart and backed it out and taken the points.

• 44:42Shaan Puri?

  Yeah, I did the same, actually.

• 44:43Speaker 00

  And like, counted the pixels. And I was like, well, you're good at your job.

• 44:46Shaan Puri?

  I did the proportions. He was like, she said 10. So if this is 10,

• 44:49Speaker 00

  Yeah.

• 44:50Shaan Puri?

  Where was she a year ago? Got 2.7 or whatever?

• 44:52Speaker 00

  Totally. He had basically done that. And that was also, you're like, that was great. It's so good at your job. So fun.

• 44:59Shaan Puri?

  Is that who you end up going with, or no?

• 45:00Speaker 00

  Uh, no.

• 45:01Shaan Puri?

  You're great, but Sequoia's gone.

• 45:03Speaker 00

  Um, 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, I mean, a beep, like, a week. And I was like, no, I am going to 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. Just fun. Right?

• 45:41Shaan Puri?

  Eric told me that he thinks you're great at negotiating.

• 45:44Speaker 00

  So funny.

• 45:44Shaan Puri?

  You said, "That's surprising to you." But he was not wishy-washy about it. He's like, "She's incredible at negotiating, one of the best I've ever been around. Ask her how or why she does it." So, no pressure.

• 45:56Speaker 00

  Yeah, no, it's truly 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, if I believe it, I won't flinch.

• 46:20Shaan Puri?

  Cool. Well, thank you for doing this. This has been amazing. Where should people find you? Find Vanta? Maybe give it a shout?

• 46:25Speaker 00

  Yeah. Vanta.com. V-A-N-T-A dot com.

• 46:31Speaker 00

  If you need any help with anything security or compliance related, we would love to help you out.

• 46:35Shaan Puri?

  Awesome. Thank you for doing this.

• 46:37Speaker 00

  Thank you so much.