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

0:00:02 And up time, my email was Christina@USV.com.
0:00:07 And it was like the right side, that USV.com is way more powerful than the left side.
0:00:08 And now you’re giving that up.
0:00:09 And so what are you?
0:00:10 You’re betting on the left side.
0:00:11 You’re betting on the left side.
0:00:12 And like, why would you do that?
0:00:15 And like, what do you think will happen here?
0:00:17 I feel like I can rule the world.
0:00:20 I know I could be what I want to.
0:00:22 I put my all in it like the days off.
0:00:25 On the road, let’s travel never to give back.
0:00:26 I don’t know if you know this fun fact.
0:00:30 You know what you, Katy Perry and Serena Williams have in common?
0:00:31 I’ve got nothing.
0:00:33 You’re all on the Forbes self-made women list.
0:00:34 I hate that list.
0:00:35 I hate that list.
0:00:36 And you are ahead of them.
0:00:37 Isn’t that kind of amazing?
0:00:38 I would have preferred that list.
0:00:39 Never existed.
0:00:40 Yes.
0:00:41 You have that Midwest modesty?
0:00:42 Yes.
0:00:44 You’re nothing good will come from that list.
0:00:45 Yeah, yeah.
0:00:49 Those lists are there, sort of made for the wrong type of people.
0:00:50 Yes.
0:00:51 Or jail time later.
0:00:52 Or something to ever the world.
0:00:53 Laugh that.
0:00:54 I was never on 30 under 30.
0:00:55 And I’m deeply glad about that now.
0:00:56 Yeah.
0:00:57 That turned out to be an anti-signal.
0:01:02 You know, when I was thinking about this episode, the way I think about it is like where you
0:01:04 are today is where a lot of people want to be.
0:01:06 You have a company that’s working.
0:01:08 It’s got like a cool startup name.
0:01:11 It’s a cool office in San Francisco.
0:01:17 Last valuation, I believe 2.45 billion, but who’s counting today you’re at where a lot
0:01:18 of people want to be.
0:01:21 But if we rewind the tape to me when I looked at your story, I think the through line for
0:01:23 this is not counting yourself out.
0:01:25 So I’m going to put that out there.
0:01:26 That might be true or might not be true.
0:01:35 But the basics of it is you had a good job and you quit to try something new, to try
0:01:38 to make it on your own, which a lot of people want to do, but they don’t take the leap.
0:01:42 You took the leap and it’s not like it hit right away and you created Vant and you created
0:01:44 this, you know, multi-billion dollar company right off the bat.
0:01:49 You did like 35 things wrong or 35 projects that went nowhere.
0:01:53 And I love that because I spent eight years of my life banging my head against the wall
0:01:58 with failure after failure after failure each time believing this is the time, you know,
0:02:01 let’s start where you have a good job.
0:02:05 You have the job at USB, which I think you kind of hustles your way into.
0:02:12 I was a stumble hustled, they announced that job like they do other jobs on the internet
0:02:19 and said, Hey, fill out this form if you want this jobs and some links to your web presence.
0:02:26 And so I literally sent them three links to my web presence and didn’t email anyone who
0:02:30 knew them, didn’t, you know, turned out I like knew people from school who didn’t pull
0:02:33 anything just sent them links and put them in a form and was like, well, now I’ll go
0:02:34 back to making slides.
0:02:36 What kind of links?
0:02:43 It was Twitter, Flickr through the era of this.
0:02:48 And I had started a design blog a couple months before and I lived in Berlin because I wanted
0:02:51 to be like a designer who lives in Berlin and those people seemed to have designed blogs
0:02:52 so I started one.
0:02:53 And that was it.
0:02:56 And they hired me.
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0:03:50 And I’ve read something that was like they, maybe Fred or somebody at the USB team was
0:03:54 telling you, you should specialize in crypto, you should become a crypto VC.
0:03:55 Is that true?
0:03:56 Kind of.
0:03:57 It’s actually I was leaving.
0:03:58 So this was end of 2012.
0:04:01 I had a lot of angst because this job was great.
0:04:02 They were great.
0:04:04 You know, like, haven’t you made it?
0:04:06 And I’m sort of like, but I don’t think I like it.
0:04:08 And again, what’s going on?
0:04:14 And one of my hangups was, you know, what have I done?
0:04:15 Why would anyone take my money?
0:04:16 Right?
0:04:19 Who’s going to take a check from me versus in my head at the time, Matt Kohler.
0:04:24 This GPU is no longer at Benchmark, but had this like illustrious Silicon Valley career
0:04:27 of like LinkedIn, Facebook, Benchmark, you know, and you’re like, me versus Matt Kohler,
0:04:30 everyone will choose Matt Kohler like a hundred out of a hundred times.
0:04:35 Which is let’s say maybe a partially imposter syndrome, but also maybe hyper logical.
0:04:36 Yeah.
0:04:38 I think like, yeah, but like also true.
0:04:42 Anyway, and I basically said that to Fred and he said two things, which, or he said
0:04:45 a couple things that are deeply insightful.
0:04:49 One was like, well, you know, you’ve got to like get over that and you can either get
0:04:54 over that by sort of out hustling people and like kind of the figure till you make a strategy.
0:04:57 And you’re sort of like, look, I’ve seen you in the office for two years, worked with
0:05:00 you for two years, like, you’re not, you’re not going to be good.
0:05:02 So you should probably shouldn’t try that one.
0:05:07 The other strategy is pick something, go deep in it and be the expert where no one else
0:05:08 is.
0:05:12 And in the fall of 2012, I recommend you choose crypto really good advice on a bunch
0:05:13 of dimensions.
0:05:16 I didn’t take it, but like, because you didn’t believe in crypto or you were just like, that’s
0:05:17 not me.
0:05:19 I’m just like, I don’t know if I want to be an investor.
0:05:20 Okay.
0:05:23 Even though it’s great and it’s wonderful and all these great attributes and like everyone
0:05:27 else wants to be a VC, but like, I want to go make things.
0:05:29 So you decided to go make things.
0:05:30 Take me back to that decision.
0:05:31 Was that easy?
0:05:32 No.
0:05:33 I’m so anxious.
0:05:34 Was everybody patting on the back and saying, you’re going to make this happen?
0:05:35 Definitely not.
0:05:39 What I did and what my plan was was I’d save my bonus from the prior year and it’s kind
0:05:42 of like a finance bonus and I was going to live off of that as long as I could.
0:05:47 So like no job, but a bunch of structure, learn to code, learn to make products, hopefully
0:05:50 something would come out of that and very much pitched as that.
0:05:53 It was not pitched as I am going to start a startup, it was pitched as I am going to
0:05:58 teach myself to code because that’s how I saw it and thought about it.
0:06:02 And like, yes, I wanted to start a startup, but I’d seen over the two years at USV, so
0:06:06 many people start startups to start them and then get into them and then be like, I don’t
0:06:11 want to work on this, but now I have people in office invested, like I can’t stop.
0:06:19 But I think there was, I think people took that conservatism as, oh, you shouldn’t be
0:06:21 doing this.
0:06:25 And so specifically, there was a bunch of like why, no one leaves USV, who has the option
0:06:27 of staying, why would you do that?
0:06:32 Or don’t you want to work at some other venture firm or oh, you want to code, why don’t you
0:06:33 go to grad school?
0:06:36 Stanford has a great graduate program in computer science.
0:06:40 Why don’t you go work for somebody else because clearly you don’t know what you want to do?
0:06:45 And then some amount of like kind of the tougher stuff, I think, or one person in particular,
0:06:48 it had been close to and who is very like, just the left side and the right side of your
0:06:49 email address.
0:06:54 And at the time, my email was Christina@USV.com and it was like the right side that USV.com
0:06:57 is way more powerful than the left side.
0:06:58 And now you’re giving that up.
0:06:59 And so what are you?
0:07:00 You’re betting on the left side.
0:07:01 You’re betting on the left side.
0:07:02 And like, why would you do that?
0:07:05 And like, what do you think will happen here?
0:07:06 So you have the good job.
0:07:07 Yep.
0:07:08 You quit.
0:07:11 You have the look, you took the right side of the email, which was the powerful part.
0:07:12 You threw it away.
0:07:15 You’re betting on the Christina part of which there are many.
0:07:18 And your plan is not even to go start a company, it’s to learn how to code.
0:07:22 And you’re going to teach yourself how to code by going on online and learning how to
0:07:23 code that way.
0:07:28 And my understanding is that worked because I went to your website, well, you have this
0:07:29 like list of projects.
0:07:30 On purpose.
0:07:31 I built all these things.
0:07:32 Yeah.
0:07:33 None of what you’ve heard of.
0:07:34 Yeah.
0:07:35 Mostly went nowhere.
0:07:36 There’s something romantic about that too.
0:07:41 Going to a cave and I’m going to reinvent myself and learn this magic superpower.
0:07:43 And I’m going to train in the mountains where nobody’s looking and then I’m going to come
0:07:44 back stronger.
0:07:45 Yeah.
0:07:46 It may not have felt that way at the time.
0:07:49 But like, I kind of knew I was supposed to feel that way.
0:07:52 And then day to day, there was some men of like, I spent more than my like daily cash
0:07:53 allow.
0:07:54 I don’t know.
0:07:58 But like, I kind of knew that’s what a better version of me would feel.
0:08:04 But practically, I knew I was a person who benefits from structure and isn’t always great
0:08:05 at doing it for myself.
0:08:11 So what I did was a friend of mine had just sold a company to eBay, New York and opened
0:08:17 up this big space in New York that was actually right across the street from the USV office.
0:08:21 And so I got up every day and I got trips for my job.
0:08:25 And I basically walked to the same place, but I went in a different door and then I
0:08:26 sat with those engineers.
0:08:28 Did you actually dress up by the way?
0:08:31 Because I feel like there’s psychologically something to actually dressing up like you’re
0:08:32 going somewhere to do something.
0:08:35 I had to dress up, but it was like I did not wear pajamas.
0:08:36 Right, right.
0:08:37 Yeah, yeah.
0:08:42 And then I go and I’d show up in the morning and I’d like do my audacity tutorial or try
0:08:49 to understand Jeno JavaScript to varying degrees and then like go home at, you know, 6 PM or
0:08:51 7 PM and then often like keep doing stuff.
0:08:56 But basically it was like tricking myself into acting like I had a job so that I got
0:08:57 up every day.
0:08:58 I was there by 9.
0:09:02 You know, I was just doing the things and I do remember there was a time my family took
0:09:07 a vacation that I went along with in January and I came back tan and I was like where were
0:09:08 you last week?
0:09:11 Like basically like why weren’t you at work and why are you tan?
0:09:15 And I would be like, I’ll complain for this, but you’re like, I want you all.
0:09:16 Everything is PTO to me.
0:09:19 But it was like also like, oh yeah, I got this.
0:09:22 Like that’s, that was kind of like a fun, fun moment too.
0:09:23 Yeah, I like that.
0:09:26 So you have this era, which is kind of like in the movies, it’s the montage.
0:09:29 It’s they just fast forward through this part takes two minutes, even though in real
0:09:32 life it’s two years and you have this thing written on your site that I love.
0:09:33 This quote.
0:09:37 And I think in my research, this was my favorite thing I pulled from you, which was at the
0:09:43 top of your site, it says, the function of the overwhelming majority of your artwork
0:09:47 is simply to teach you how to make the small fraction of your artwork that soars.
0:09:50 And this is from a book called the art of fear.
0:09:51 Can you, I love that.
0:09:52 Can you, can you explain that?
0:09:53 Yeah.
0:09:57 I think it’s deeply true of creative projects and I think startups or businesses or, you
0:10:01 know, internet art is like they’re all creative projects.
0:10:06 One thing I learned at USV, seeing, seeing people bitch, but then like hearing the stories
0:10:10 behind their big, you know, Tumblr, Twitter, force square, whatever, all the big successes
0:10:15 of the era were when I walked into USV, I was like, everyone is Mark Zuckerberg.
0:10:19 Not actually, but like everyone, you know, like startup founders or people who have an
0:10:23 idea and they go into their room and they build it and everyone uses it.
0:10:26 And it’s like the first or second thing they’ve done and like Facebook bigger, but that’s
0:10:27 kind of all of Mark’s projects.
0:10:31 And so like, that’s the way it, you know, I’m like, shoot, I’m like, not, it’s never
0:10:32 worked for me.
0:10:34 So I’m probably not one of them.
0:10:38 And USV was just so helpful in disabusing that notion and being like, look, some people,
0:10:41 like a very small number of people can do that.
0:10:42 And that’s incredible.
0:10:43 I wish I were them.
0:10:44 I’m not.
0:10:52 Most people actually try a bunch of stuff and eventually something might work.
0:10:57 But it’s like, at best thing five and it might be thing 55.
0:11:01 But no one really talks about that because it’s both because it’s like painful and kind
0:11:02 of not fun.
0:11:04 And, you know, it’s supposed to be romantic, but actually it just kind of sucked in hungry
0:11:09 for two years, literally and metaphorically.
0:11:13 And it’s so much nicer, like you get so much praise for sort of being like the brilliant
0:11:14 person.
0:11:15 Right.
0:11:16 And that’s the expectation too.
0:11:21 I think I just had a like, well, yeah, but like that’s discouraging so many people from
0:11:22 starting.
0:11:25 It’s sort of like when you watch a bunch of movies about love and then you’re like, this
0:11:26 is what it’s like.
0:11:27 Yeah.
0:11:28 I will bump into a stranger.
0:11:29 Our papers will fall on the floor.
0:11:30 We’ll swap a paper.
0:11:31 We’ll swap a paper.
0:11:32 You’ll have to come finally.
0:11:35 But then I’m not into him, but he just pursues me anyway.
0:11:38 And it’s like, if you have that notion that that’s how it goes, you’ll almost count yourself
0:11:40 out of other things that could have worked otherwise.
0:11:41 Yes.
0:11:44 And if you watch the social network, you’re like, that’s just how it is.
0:11:51 Brilliant genius has a vision, does it, takes off, and then he rides that bull at the rodeo.
0:11:55 We actually, after I read this quote on my team, we started using this phrase just called
0:11:56 bad art.
0:11:59 So I’ll hit up my team in the morning, I’ll say, hey, let’s make some bad art.
0:12:03 Like intentionally, just almost lower the stakes instead of, we have to find the next
0:12:06 big winner idea, let’s just make some bad art today.
0:12:10 And the analogy I gave them, I said, imagine like, you go to a hotel or a motel, you’re
0:12:13 doing something, you’re going to a place that you’ve never been before, maybe nobody’s been
0:12:14 there before.
0:12:17 When you turn on the tap, like it’s muddy water at the beginning.
0:12:20 If you look at that and you’re, it’s like, you’re mortified by it, it’s disgusting.
0:12:25 You turn it off right away and be like, you bad leaf.
0:12:29 But if you know that actually that’s the process, that you sort of have this muddy water of bad
0:12:33 ideas and bad skills at the beginning, get it out of your system, then suddenly the water
0:12:34 starts running clean.
0:12:38 And I think that framework is, is just very useful for anyone who’s doing either creative
0:12:42 endeavors or startups, which are a pretty creative endeavor too.
0:12:44 Do you know the story about making pots?
0:12:45 No.
0:12:46 From the same book.
0:12:50 So, and I think it was like around the chapter that quote was, but anyway, there’s an art
0:12:57 teacher and he said, okay, art school pottery class, you have one assignment all semester.
0:13:01 You have five weeks to make the perfect pot.
0:13:05 You can turn in as many pots as you want, but I will judge them all and the highest grade
0:13:08 will go to the person who has the best pot.
0:13:15 And student one spends all semester crafting the perfect pot and hands it in at the end.
0:13:21 And student two makes two pots a day and they’re all back for a long time, right.
0:13:24 But over the course of semester and hands in whatever, like 300 pots and like who gets
0:13:25 a better grade.
0:13:26 Of course.
0:13:27 300.
0:13:28 Right.
0:13:29 Yeah.
0:13:30 Yeah.
0:13:31 But it’s like that concept.
0:13:32 Yeah.
0:13:33 It’s like so true.
0:13:34 And you have to live it almost to really internalize it.
0:13:35 Yeah.
0:13:36 Actually a great thing I did once with my company, there’s, you’ve probably seen like the marshmallow
0:13:40 test or like the psych test with kids, it makes a good point, which is you give a bunch of
0:13:45 supplies to, you break your team into a bunch of groups, groups of maybe four or five.
0:13:51 And they get like sticks of spaghetti, one marshmallow, and there’s something like maybe
0:13:54 a string and like two other things, like a piece of tape.
0:13:58 And so the idea is, hey, give an hour at the end of the hour, I will come around, I will
0:14:02 measure whoever from the tabletop has the highest marshmallow.
0:14:05 So whoever could build the biggest tower wins.
0:14:09 And what most people do, what my team did and everybody who does this the first time
0:14:14 pretty much is you immediately go into like the way we do most things in corporate life.
0:14:19 So it’s kind of like, okay, you’re in charge, you do this, you sort of segregation of duties,
0:14:21 you start trying to like plan.
0:14:24 And then you, so you sketch a little bit, then you start building the tower and at the
0:14:28 very end, you’re like, okay, okay, what’s almost time, put the marshmallow on.
0:14:32 And the entire thing collapses because even though a marshmallow looks so small and like
0:14:35 light compared to spaghetti sticks, it’s way too heavy.
0:14:40 And you don’t realize that because you didn’t like, you like back loaded the possible failure,
0:14:45 you know, the failure mode or the sort of test of the idea.
0:14:49 You spend all your time kind of planning and architecting this brilliant, beautiful thing.
0:14:53 And the cool thing that they’ve shown in this is that when they do it with kids versus adults,
0:14:57 the kids right away either eat the marshmallow or put the marshmallow on right away.
0:14:58 And they’re like, oh, it’s too heavy.
0:15:01 You have to have like five spaghetti sticks to hold this thing up.
0:15:03 They figure that out right away.
0:15:05 They don’t kind of save that to the end to try to perfect it.
0:15:11 And that sort of iterative thing about testing the riskiest assumption is maybe important.
0:15:16 It seems like for you, did you make that mistake of kind of like, over analyzing, over planning
0:15:18 at the beginning, like not testing with customers?
0:15:23 Less the very beginning, because at the beginning I was just, I built a book website.
0:15:26 It was like good reads, but better, but it was actually worse because I didn’t notice
0:15:27 doing.
0:15:30 But like it was something for me.
0:15:35 This confused everyone else, right, because they’d be like, well, you’re not, you know,
0:15:36 what are you doing without having a job?
0:15:38 And I’m like, I’m building a book website.
0:15:40 And they’d be like, are you going to compete with Amazon?
0:15:41 No.
0:15:42 Like, are you going to compete with Goodreads?
0:15:45 And you’re like, well, you know, with my, with my friends, but like, no, you know, and
0:15:48 then they’d be like, well, what would you say you’re doing, you know, and you’re like
0:15:52 mostly battling JavaScript errors, trying to end and like spending less time on Stack Overflow.
0:15:55 You know, in many ways, this is a whole confusing thing.
0:15:59 But the beginning, it was just, I like, like when I would go visit a friend’s apartment,
0:16:00 I’d always like be drawn to their bookshelf.
0:16:01 You want to see what’s on their bookshelf?
0:16:04 Anyway, so I was like, okay, what if I can get everybody’s books online?
0:16:07 But he was like, clearly, this is not a business.
0:16:11 Like best case, I’m making like 50 bucks a month, you know, Amazon referral fees, like
0:16:12 not a business.
0:16:13 But you did it anyways.
0:16:14 Why?
0:16:15 Because I wanted it.
0:16:19 I want, and it was a good, it wasn’t, you know, like you do your initial coding tutorials
0:16:22 and you like are making whatever the other person wants to make, which is not what you
0:16:23 want to make.
0:16:25 And like, I actually wanted this thing.
0:16:29 And it like forced me to be like, oh, you know, now I want like an animation when you
0:16:30 shelve the book.
0:16:31 So you’re right.
0:16:36 Like learn about CSS animations, whatever it is.
0:16:40 Hey, let’s take a quick break to talk about another podcast that you should check out.
0:16:42 It is called the next wave.
0:16:45 It’s hosted by Matt Wolf and Nathan Lanz as part of the HubSpot podcast network, which
0:16:49 of course is your audio destination for business professionals like you.
0:16:52 You can catch the next wave with Matt Wolf and he’s talking about where the puck is
0:16:57 going with AI creators, AI technology and how you can apply it to your growing business.
0:16:58 So check it out.
0:17:04 I’ll listen to the next wave wherever you get the podcast.
0:17:06 And so you, so you started building stuff for yourself.
0:17:07 Yep.
0:17:10 Did you ever switch gears to, okay, now, now I’m going to do the startup startup.
0:17:15 I’m going to do the thing that might actually, you know, get me out of poverty, self-induced
0:17:16 poverty.
0:17:17 Yeah.
0:17:20 So at that point, I was very like, look, I, you know, just taught myself how to code
0:17:22 and like, you know, am I that good?
0:17:27 No, but learning how to do some of this is much harder than it should be.
0:17:30 And a lot of it’s because their programming tools make us like hold everything in our
0:17:34 heads and you have to teach yourself to think like a computer and like read through code,
0:17:37 which is like, not how a person, you know, you think like a computer.
0:17:41 And once you have that, everything gets easier, but like, why?
0:17:43 We are typing on computers.
0:17:47 And so I kind of got on this, like, if we could make our programming environments better,
0:17:51 you can like more, they will just make more sense and more people will like learn to code.
0:17:54 And so, you know, I was really into that personal problem.
0:17:58 So the like, you know, live in the future and build back, you know, whatever all the startup
0:17:59 trope advice.
0:18:00 I’m curious about that.
0:18:02 What startup trope advice actually helped you?
0:18:08 I think the build something you want is a bit of a red herring.
0:18:12 It works in some cases, but you’re also very limited to your experience.
0:18:15 It’s kind of like when they tell writers, write what you know, and then you like, you
0:18:18 know, it’s like a 14 year old who’s had a charmed life and like, they just don’t know
0:18:19 that much.
0:18:21 And so like, what are they going to write about?
0:18:26 And so, my version of that is like, look, if there is something personally meaningful,
0:18:28 like, by all means go for it.
0:18:29 That’s top ranked.
0:18:30 Totally.
0:18:35 But like second best is like, find someone else with the problem and deeply, deeply understand
0:18:36 them.
0:18:41 I think there’s a very, the shut your eyes, imagine the future.
0:18:42 What’s it look like?
0:18:43 Build that.
0:18:45 I think this makes sense in retrospect.
0:18:49 I think in the moment, it’s pretty hard to generate reasonable startup ideas during that.
0:18:50 Right.
0:18:51 Yeah.
0:18:55 I can tell you a story about Vanta where Vanta fits that and it does, but it’s in retrospect.
0:18:56 Yeah.
0:19:00 So what was the actual in the moment way that you stumbled into this idea of Vanta that
0:19:04 now seems obvious as all great ideas do once they exist.
0:19:08 And now there’s you guys and some competitors trying to do the same thing, but that was kind
0:19:12 of a novel idea and it was a new part of the market at least.
0:19:14 What was the insight for that?
0:19:19 The insight was wanting to start a security company that started serving startups.
0:19:23 There seemed to be like security with this huge market, but no one was really focused
0:19:25 on startups and sort of didn’t use security tools.
0:19:29 And I’m sort of like, why and when does this become a 90 quadrillion like go from a zero
0:19:33 TAM to like 90 quadrillion dollar market science in precise terms.
0:19:34 Yeah.
0:19:35 That’s the official number.
0:19:36 Yeah.
0:19:37 Exactly.
0:19:38 But wait, why security?
0:19:40 Cause like, you know, when I’m talking, I’ve been talking to you for, I don’t know, 20 minutes
0:19:44 now, you don’t strike me as somebody who’s like, I wake up every morning and I was thinking
0:19:46 about security during that year off.
0:19:49 Why did you even think about security to begin with?
0:19:50 It seemed really interesting.
0:19:55 It seemed like this kind of competitive cat and mouse thing where they, uh, with attackers
0:19:57 where there’s like kind of a real dashboard.
0:19:58 Right.
0:20:00 I mean, one of the things I’ve, I mean, I guess I knew, but I didn’t really know.
0:20:05 Like I’m very competitive, should have played more sports as a kid didn’t, uh, through Vanta
0:20:08 have an outlet for a lot of that energy, which is great.
0:20:12 And I think honestly, when I was at Dropbox, I worked with this product security team and
0:20:13 they were great.
0:20:18 They were super fun and they were really good educators and it’s not like they’d hosted,
0:20:19 you know, seminars on things.
0:20:22 It’s just like, they wanted you to fix something, but they’d come over and sit next to you
0:20:26 and explain why it was important and how and all the, anyway, they were just great.
0:20:31 And so in coming up with startup ideas, there was a bit of like, well, this actually seems
0:20:35 like a deep enough, interesting enough space that if I work in it for years, there’ll be
0:20:36 lots of things.
0:20:40 And if I can’t come up with anything and end up burning, you know, 18 months of my life
0:20:43 learning about security on the internet, it could have been worse.
0:20:44 Yeah.
0:20:45 Right.
0:20:47 Like you kind of look back and be like, okay, worst case, nothing comes out of this, but
0:20:49 like, I, you know, I’ll feel as good as I will.
0:20:50 Well, connect the dots for me.
0:20:55 So you, you took the year or multiple years off to teach yourself two years.
0:20:56 Yeah.
0:20:57 But then you go to Dropbox.
0:20:58 Yeah.
0:20:59 So you go back to getting a job.
0:21:00 Yeah.
0:21:02 So I feel like we, like there’s a part of the story that’s like, I iterated, I finally
0:21:03 found it.
0:21:04 No, no, no.
0:21:05 Finally, you found a job at Dropbox.
0:21:06 Yeah.
0:21:10 Cause I was kind of like, okay, now I can code, but I’ve never had a real job.
0:21:12 I’ve never worked at a company.
0:21:13 Never worked with people.
0:21:17 Also, my, my like friends are kind of getting promoted and like, I can, you know, like it’s
0:21:22 unclear if I’m employable, you know, like this seems bad.
0:21:26 And I was really frustrated because again, like, I wouldn’t tell people I wanted to start
0:21:31 up to come out of that, but like I did, but I also at the time was like, well, nothing
0:21:32 I’ve worked on should be a startup.
0:21:33 Right.
0:21:34 So like.
0:21:35 So what was that story you told yourself?
0:21:38 So you, you spent the two years, you bet on yourself.
0:21:39 Yeah.
0:21:40 Which sounds amazing.
0:21:41 That’s a great t-shirt.
0:21:42 Bet on yourself.
0:21:43 Yeah.
0:21:48 I told you, I did it for eight years and I was delusional enough to keep going, but also
0:21:54 objectively it was bad and I should have, I had to tell myself certain stories in order
0:22:00 to either a keep going or to like just maintain a self, a sense of confidence beyond that
0:22:02 because the evidence was telling me, you suck.
0:22:03 Yeah.
0:22:04 And I just couldn’t tell myself you suck.
0:22:05 Cause then I definitely suck.
0:22:06 Yeah.
0:22:10 What were you saying when the evidence kind of said, you suck?
0:22:11 This was very silly.
0:22:16 I had this like survey, I would fill out a Google form, I’d fill out for myself every
0:22:19 Sunday or every weekend.
0:22:20 What are you working on?
0:22:21 How do you feel about it?
0:22:22 What are you going to do?
0:22:23 Like what’s your next goal?
0:22:24 What are you going to move forward?
0:22:25 You made that for yourself.
0:22:26 Made it for myself.
0:22:27 It was like a personal accountability thing.
0:22:28 Right.
0:22:29 Okay.
0:22:30 And I asked a bunch of questions.
0:22:31 They were all useless.
0:22:34 The only question that ended up mattering was what would make you stop working on what
0:22:36 you’re working on right now?
0:22:40 And to your point, it turns out my present self always thinks I should keep going, but
0:22:44 my past self sometimes thinks current self should stop, right?
0:22:49 And so it’s actually like looking at those answers and being like two months ago, I said
0:22:53 I should stop if I got to the point I meant now.
0:22:55 I don’t actually think I have counter-revealing evidence.
0:23:00 I just have stubbornness, shoot, I should probably stop.
0:23:01 And so that’s how you were stopping those projects.
0:23:02 Yeah.
0:23:08 I sent you some questions ahead of this to try to understand what you think is important
0:23:09 to talk about.
0:23:10 What do you think is insightful?
0:23:15 I think you said something that I really resonate with, which is managing your own mind, managing
0:23:18 your own psychology is one of the most important things.
0:23:19 Yep.
0:23:20 How does one do that?
0:23:23 And how would you teach that to somebody else or how would you talk about that to somebody
0:23:24 else?
0:23:26 I think hard to do, hard to teach.
0:23:35 I think what I try to tell people is figure out what, like it’s personal and not personal
0:23:43 sensitive, but like personal, like specific to you and figure out what makes you happy
0:23:49 or centered, whatever those things are and like do not give them.
0:23:53 And so for me, for years, there was like a, you know, running three or four times a week
0:23:54 and like exercise.
0:23:55 Sure.
0:24:00 But it was actually just like the mind clearing catharsis kind of meditative, like running.
0:24:04 And you know, it was like running for me, but like whatever for someone else.
0:24:09 And it’s like whatever that thing is, do not give it up and I don’t care how busy you get.
0:24:15 But sort of know what makes you feel like you and don’t drop those things.
0:24:18 Know what things make you feel like you, which is kind of like what you’re talking about
0:24:19 is habits and hobbies.
0:24:20 Is that more of what you’re thinking about?
0:24:23 And it’s just like that feeling where you’re like, you’re like moving through the world
0:24:26 and you like feel like you’re at your best, you know, like you’re the best, shiniest version
0:24:27 of yourself.
0:24:29 It’s like, what brings that on?
0:24:31 So for you, running is one.
0:24:32 What else?
0:24:33 Running was one.
0:24:37 It was like not in any, I mean, kind of an elegant intellectual, but actually just because
0:24:40 it is something I have done since I was six years old, right?
0:24:43 And so like, if I think of like hobbies or anything I’ve done through my life reading,
0:24:46 it was actually one of the biggest through lines.
0:24:48 And so there’s a part of that that just feels like me.
0:24:49 Yeah.
0:24:52 Because I was looking, you read like, I don’t know, 30, 50 books a year or something.
0:24:53 Yeah.
0:24:56 But it’s like, and yes, I want to learn things and like blah, blah, blah, but actually it’s
0:24:57 just like it is centering.
0:24:58 I feel like me.
0:24:59 How do you do that?
0:25:03 Mine was running a company and, and by the way, mine was not a $2.45 billion company.
0:25:05 I was like, I have no time to read.
0:25:06 Are you kidding me?
0:25:07 There’s problems everywhere.
0:25:08 I’m drowning in problems.
0:25:11 And did you just replace TV with reading or something as simple as that?
0:25:12 Yeah.
0:25:13 Like, actually.
0:25:17 Eric told me that you are like extremely quick with reading.
0:25:19 He’s like, she would take a bus to work.
0:25:20 Yeah.
0:25:21 And read the book.
0:25:22 And read the whole book on the bus ride.
0:25:23 Oh, yeah.
0:25:24 I mean, over the course of a week or so.
0:25:25 But yeah, like, actually to this day, I still take…
0:25:26 The way he said it was more legendary.
0:25:29 He was like, to and from, cover to cover.
0:25:30 No.
0:25:31 I wasn’t at it.
0:25:35 I’m going to actually, I actually still take a bus to work part of it so I can just sit
0:25:36 there and like…
0:25:37 You bus to work.
0:25:38 Yeah.
0:25:41 Cause look, if I take a car, I’m just going to like sit in the back with my laptop writing
0:25:45 emails, you know, and then a bus like, oh, let’s just go bus, I’m not pulling on my laptop
0:25:46 on that.
0:25:48 Unless something’s like really gone wrong.
0:25:54 And so it just forces me to like sit there and have 20 minutes between home and work.
0:25:55 And I like that.
0:25:57 Like, you know, people are like obsessed with cold plunges.
0:25:58 Yes.
0:26:00 I think the more hardcore version is take a San Francisco bus to work.
0:26:04 It’s like, wow, you can endure a 18 minute bus ride with like…
0:26:05 Buses aren’t bad.
0:26:07 5R used to be my bus.
0:26:08 5R is a great bus.
0:26:11 Dude, I used to take the 38 and the 38 is like an actual zoo.
0:26:12 It’s like…
0:26:13 Anything can happen.
0:26:14 Yeah, yeah, yeah.
0:26:15 No 5R.
0:26:16 Great bus.
0:26:17 I miss it.
0:26:18 I miss it.
0:26:19 Okay.
0:26:23 So Banjino psychology said, figure out what makes you feel like you, most of you, and
0:26:25 make sure you stick with those things.
0:26:26 Keep doing those things.
0:26:28 It’ll kind of keep you centered with it.
0:26:33 What about banjino psychology when it comes to self doubt, when it comes to getting down
0:26:34 on yourself?
0:26:35 Because I spent two years.
0:26:37 I didn’t really land where I wanted to land with it.
0:26:40 Did you have a conversation with yourself there or a story you told yourself in order
0:26:41 to…
0:26:42 Yeah.
0:26:43 I was so annoyed.
0:26:46 I was, which in retrospect, I was like being so pretentious.
0:26:47 Like life was good.
0:26:52 You know, again, like the, the bat nut, like my worst case outcome was becoming a product
0:26:53 manager at Dropbox.
0:26:54 The height of Dropbox is power.
0:26:55 Like my life was great.
0:26:56 Could you just say the bat nut?
0:26:57 Yeah.
0:26:58 Right.
0:26:59 But like my life was great.
0:27:00 It did not feel great at the time.
0:27:01 It was totally great.
0:27:05 And again, I knew I was like 5% aware of that 10%, but that was not the lived feeling.
0:27:07 Do you use negotiation terms like that just regularly?
0:27:08 Hopefully not.
0:27:09 That sounds kind of obnoxious.
0:27:10 I’ll try not to now.
0:27:11 No, I like that.
0:27:12 And…
0:27:16 I’ve always felt that if you build a great Silicon Valley company, internally in your
0:27:18 company, you should be a totally normal person.
0:27:21 But outside you should have that like 10% crazy.
0:27:22 Yeah.
0:27:25 Because you like actually like 2X the valuation, it just like creates this extra aura.
0:27:26 It’s like…
0:27:27 It’s totally true.
0:27:28 Wow.
0:27:29 She’s barefoot all the time.
0:27:30 Interesting.
0:27:31 It must be one of those real outlier types.
0:27:32 Oh my gosh.
0:27:33 All right.
0:27:34 I want to ask you about this list of ideas that you did.
0:27:40 So I’ve looked back in my career and even when I went through eras where I tried something
0:27:43 and it didn’t work, a lot of the times I look back with the benefit of hindsight now and
0:27:46 I think, oh, I was just sort of an idiot about it.
0:27:50 Had I actually either stuck with it or done it differently or pivoted the market, that
0:27:51 actually was a good idea.
0:27:54 I’m curious, do you feel that way about any of the projects you worked on?
0:28:00 Like there are projects and I say that with deep love, but like they’re not businesses.
0:28:03 The voice assistant for biologists, yeah, that doesn’t sound like a great business.
0:28:04 That was just comically bad.
0:28:05 No, yeah.
0:28:11 There was like a deep lack of any commercials and nearly everything on that list, which
0:28:17 I think is part of why Vanta has had commercials like baked in from the very beginning because
0:28:20 I’d made that mistake so many times.
0:28:21 What about now?
0:28:27 So if you weren’t doing this or in general, when you operate a business, you see a bunch
0:28:33 of pain points, blind spots, maybe parts of the market that are unaddressed.
0:28:37 If somebody’s listening to this right now and they are looking for inspiration or ideas
0:28:42 that spark thoughts in their head about stuff that they could go do, what would you recommend
0:28:44 people think about?
0:28:46 What problems do you think need solving?
0:28:53 Yeah, I think so much of what I think about that’s not kind of directly in Vanta’s wheelhouse
0:28:58 is something around like running a B2B SaaS or being in a B2B SaaS business, forget running
0:28:59 it just being in it.
0:29:02 There’s like someone please fix the go-to-market tooling stack.
0:29:06 There’s 9,000 tools and it’s like you jerry-wing them together in this Rube Goldberg machine
0:29:11 and the marbles are all up on the floor and like anyone wants a B2B SaaS, just like fix
0:29:15 that, go full stack on all that, but for people who don’t want B2B SaaS, which there are hopefully
0:29:22 many, I think the process Vanta came out of, I mean I liked it going in, but of course
0:29:28 I really like it, but that was pick something you want to learn about and just go talk to
0:29:32 anyone you can about like what their days are like, what their problems are like, just
0:29:37 like what’s going on and kind of try to develop a mental model of the space.
0:29:42 The story I heard about Vanta, which sometimes we make up these retrospect stories, I don’t
0:29:43 know, you tell you can-
0:29:45 I can actually tell that the true one.
0:29:49 Like blink twice if it’s true and whatever, but you’re at Dropbox, you work on this thing
0:29:52 called Paper, which was this, I remember like seeing Paper at the time, it was like this
0:29:55 idea of this like collaboration tool and you go to-
0:29:56 Dropbox is version of Google Docs.
0:29:57 Yeah, Dropbox is Google Docs.
0:30:02 You go to launch it and it’s like, hey, we don’t have SOC too, so can’t really launch
0:30:04 or customers can’t use it and you were like, SOC what?
0:30:05 Yep.
0:30:08 And you didn’t know really what that was and you were like, so how do we get that?
0:30:12 And you started asking questions to try to understand like what is this thing that blocked
0:30:13 us here?
0:30:18 If it blocked us, maybe it blocks other people, Dropbox had a security team that was going
0:30:22 to be able to try to solve those problems, but like the average startup doesn’t.
0:30:26 And the next part of the story that I liked was even though you had just spent two years
0:30:31 learning to code and built 35 projects and coded them up and shipped them out there or
0:30:33 whatever, you didn’t write code for this.
0:30:37 You were like, I’m going to test this idea with an Excel spreadsheet only.
0:30:41 And you went to one or two startups, I think YC startups that you thought might need this
0:30:44 and you were like, hey, if I did this for you, would that be valuable?
0:30:47 And they’re like, oh yeah, sure, can you, how much of that is true?
0:30:48 All true.
0:30:49 All right.
0:30:55 A quick break, I know that if you’re listening to my first million, that means you love numbers.
0:30:59 Well, I’ve got a new podcast called Moneywise and the premise is simple.
0:31:00 We talk to high net worth people.
0:31:06 So people who have somewhere between 50 to 500 million dollars and we start with simple
0:31:10 premise, which is tell me exactly how much money you have, how much money you make every
0:31:15 month, what your portfolio looks like, how much money you spend every month and every
0:31:20 other bit of information that involves your net worth and your spending.
0:31:24 And the reason we do this is because I want to demystify money.
0:31:29 So we just had this woman named Anne who has a $94 million portfolio after selling her
0:31:33 business and she spends $360,000 a month and she talks about where the money is and what
0:31:37 she spends it on and why she spends that much and if it makes her happy or not.
0:31:41 And then we dive deep on different topics like children buying versus renting, giving
0:31:42 money away.
0:31:45 We basically are having a conversation that I see a lot of rich people having behind
0:31:46 closed doors.
0:31:47 We do it publicly.
0:31:48 So check it out.
0:31:54 It’s called Moneywise and you can find it wherever you get your podcasts.
0:31:57 The stylized part is all the drop books have happened.
0:31:58 There was no light bulb.
0:32:01 I was like, not smart enough to have a light bulb go over my head at the end.
0:32:02 Wish so.
0:32:05 But it was just like learned about the whole process, learned what it would take.
0:32:09 And then like basically ran screaming from the room because it just sounded awful, especially
0:32:12 when we were trying to launch and even figure out if we had product market fit.
0:32:15 So the idea of like, we’re going to go two years of work to then see if we have product
0:32:16 market fit.
0:32:17 You’re like, bad, bad.
0:32:19 Like, how do I find reality faster?
0:32:22 Came back to it later, did the spreadsheet thing and I think honestly, it’s like because
0:32:23 it’s sort of five things on the list.
0:32:26 Like kind of at the point where you’re like, okay, I can write, you know, maybe someone
0:32:27 shoddy job.
0:32:32 But like I can code the thing or code a first version of the thing.
0:32:33 That’s not the hard part.
0:32:36 The hard part is, does anyone want my thing at the end?
0:32:40 And so like how much of the validation can you front load there?
0:32:44 So I think a lot of people hear that and they’re like, they hear you should talk to customers.
0:32:46 You should validate people want this, make something people want.
0:32:47 Yeah.
0:32:50 I don’t think anyone has any idea how to actually do it.
0:32:53 So what is the quick and dirty recipe for how you actually go?
0:32:55 Who do you talk to?
0:32:56 What do you really ask them?
0:32:59 How do you make sure you’re not getting these false positives just by being like eager beaver
0:33:04 and they’re like, yeah, that would be, maybe I’d be interested and you’re like, they totally
0:33:05 loved it.
0:33:06 Yeah.
0:33:10 So on the false positives, anything that is not, can you do this for me now tomorrow
0:33:12 next week is a no.
0:33:16 And people are really kind and they want to be kind and so they don’t say like rarely
0:33:20 do they say no, but a lot of like, oh, maybe next quarter or like, I don’t need this, but
0:33:27 my friend, my hard notes, you should date my friend knows totally hard nose.
0:33:31 I think on who to talk to, I mean, look, we started with like anyone who talked to us
0:33:36 and then it was just like, and that sort of ended up being co-workers, former co-workers
0:33:40 because you had like some like, well, I don’t know if you know anything about this topic,
0:33:41 but you’re kind of a nice person.
0:33:44 And so I’ll like give you a half an hour sort of thing.
0:33:48 And then just fan out from there at the end when they’re like, well, you know, you ask
0:33:49 them, do you have anybody else?
0:33:53 And they list people and like, say yes, follow up with customized emails, like it forward,
0:33:57 you know, like make it easy for them and just keep going out.
0:33:58 Yeah.
0:34:01 I think that’s an important one, make it easy for them to do the thing they said they want
0:34:02 to do.
0:34:03 Oh yeah.
0:34:04 Like follow up and be like, thanks so much for meeting me.
0:34:07 Like I would love to talk to your friend who Eric, who said this, like here’s what I’m
0:34:08 working on.
0:34:10 Like, and just like assume they will, like write them in email.
0:34:11 They will forward.
0:34:12 Exactly.
0:34:13 Yeah.
0:34:15 So you have you ever read this thing called the mom test?
0:34:16 Yes.
0:34:18 Do you subscribe to that?
0:34:19 Yeah.
0:34:20 Generally.
0:34:21 Yeah.
0:34:25 I don’t even actually remember what was in the book, only one line, which was they can’t
0:34:28 tell you about the solution, but they can tell you about their problems.
0:34:31 So all your questions need to be first about their problem.
0:34:35 And then at the end, if you want to ask them about your solution, great.
0:34:38 But just assume they don’t really know what the solution needs to look.
0:34:39 Yeah.
0:34:40 I think that’s true.
0:34:44 Try to avoid yes/no questions, which is harder than it sounds.
0:34:49 And there’s a bunch of kind of user research tips, tricks of like if somebody mispronounces
0:34:52 something, go with their pronunciation, because otherwise they’re going to like…
0:34:53 Don’t break rapport.
0:34:54 Exactly.
0:34:55 Exactly.
0:34:56 Like a lot of bad…
0:34:57 Yeah, that’s true.
0:34:58 I think I do that.
0:35:00 And it sort of is like a problem because it’s kind of a know-it-all move.
0:35:01 Right.
0:35:04 And then it makes them feel like their mind goes over there.
0:35:05 Exactly.
0:35:06 Oh, am I being stupid?
0:35:07 Did I say something stupid?
0:35:08 Exactly.
0:35:10 Or you just like want them to like stream of consciousness at you, basically.
0:35:11 Yeah, exactly.
0:35:15 Do you have any good hustle stories for how Vanta kind of got the flywheel going?
0:35:20 Because you know, starps don’t kind of like explode right away necessarily.
0:35:24 And I’ve seen your like ARR chart, which looks like a beautiful hockey stick.
0:35:25 Yeah, totally.
0:35:28 But if you zoom in, it’s like, wow, that was a year where it’s like pretty kind of small.
0:35:31 And then I started to accelerate.
0:35:37 Was there anything you did that you felt was interesting, unique, that kind of took us
0:35:38 over to creativity?
0:35:39 Interesting.
0:35:43 It’s so funny looking back because like I sent a bunch of outbound emails to IC companies,
0:35:45 but I didn’t know the word outbound at the time.
0:35:46 Right?
0:35:49 I was like emailing YC founders for feedback and I legitimately did want their feedback
0:35:50 kind of to this.
0:35:56 But it was like half a like, okay, I’m going to spend, you know, 60, 70% of the call talking
0:35:58 about the problem and how you’re solving it.
0:36:02 And then the end be like, I am building a thing, would you like to hear about it?
0:36:03 But it was like totally cold outbound.
0:36:04 You know, I just like didn’t know that word.
0:36:07 So you emailed a bunch of YC people, that got the ball rolling.
0:36:08 What happened after that?
0:36:09 Yeah.
0:36:15 So the early strategy was like just do and try everything and then see what works.
0:36:16 So what did work?
0:36:17 That outbound worked.
0:36:19 There was a word of mouth.
0:36:24 We tried actually really hard in the early days to basically build this call response
0:36:28 and like founder Slack channels or VC Slack channels where someone said, “Sock too.”
0:36:30 And someone else would say, “Vanta.”
0:36:31 And you just wanted this, you know.
0:36:32 And how do you do that?
0:36:34 You’re saying like build the brand in people’s mind.
0:36:35 Yeah.
0:36:37 That was great for a while.
0:36:42 And then a bunch of knockoffs came and there was a bunch of other ways to get stuck too.
0:36:43 And so that association…
0:36:48 I remember you guys in the billboard, there’s like, what is it, compliance that doesn’t
0:36:49 suck too much?
0:36:50 Yep.
0:36:51 Still up.
0:36:52 Yeah.
0:36:53 That was good.
0:36:54 Still up.
0:36:55 Yeah.
0:36:56 I joke with people.
0:36:58 Like we make software, but like we also make a billboard and we’re equally known for
0:36:59 both.
0:37:04 We’re like equally as important.
0:37:05 What else?
0:37:10 Podcast advertising really worked in, I mean, actually it still really works, but like really
0:37:12 worked in the early days.
0:37:15 I thought podcast advertising was just gonna be like sending money out the window.
0:37:17 I was totally wrong.
0:37:18 And that’s what happened.
0:37:19 Somebody on your team pitches you this.
0:37:20 Eric pitches you this.
0:37:25 Eric was like, “I want 20K, go on Twitter, this weekend startups or something.”
0:37:29 And I like rolled my eyes and said, “Fine, whatever, go.”
0:37:30 She totally worked.
0:37:31 She was totally right.
0:37:35 Eric is like this mythical figure to me now where I’ve only ever heard great Eric stories.
0:37:37 And so I don’t want to hear any…
0:37:40 If anybody has a bad Eric story or an idea you had that did turn out true, don’t tell
0:37:41 me please.
0:37:42 No.
0:37:45 All right, I want to ask you about a couple other of your controversial or maybe just
0:37:48 less consensus opinions.
0:37:50 I’ve seen you write these somewhere on the internet.
0:37:53 You tell me if you still believe these and why.
0:37:54 Consistency is overrated.
0:37:55 It’s on your website.
0:37:56 Oh, yeah.
0:37:57 People read a lot into this.
0:38:00 I’m just joking with myself because I say, “Contact me through these four ways that
0:38:02 are all of totally different names on them.”
0:38:03 Oh, okay.
0:38:04 So like it’s just like minor…
0:38:05 Naming consistency is overrated.
0:38:10 Yeah, it’s just like minor self-awareness thing that I think people think is meant
0:38:12 to be a broad philosophical statement.
0:38:14 Do I actually think it’s a broad philosophical statement?
0:38:15 No, probably not.
0:38:18 I think Vantas taught me consistency is actually underrated.
0:38:22 Yeah, I was gonna say, you strike me as somebody who’s consistency first.
0:38:23 Yeah.
0:38:25 It’s bad when the goalposts move.
0:38:28 I don’t know if you’re saying you think this or that other people think this.
0:38:32 I think other people, the advice tends to be if your goalposts keep moving, it’s hard
0:38:34 to find happiness and you’re always something happiness.
0:38:35 Explain what it means.
0:38:36 So what does that even mean?
0:38:37 The goalposts moving.
0:38:38 Yeah.
0:38:43 I mean, it’s a lot of forms of life, but let’s take startup founders just because you want
0:38:45 to start a company.
0:38:46 You want to hire some people.
0:38:47 You want to get to seed round.
0:38:50 You want to get to a million in ARR, but then by the time you get there, you’re like, “Actually,
0:38:51 I want to get to 10.”
0:38:52 That’s it?
0:38:53 Yeah.
0:38:59 The goal is something you are chasing, and I think that is generally seen as a recipe
0:39:00 for unhappiness.
0:39:01 Right?
0:39:03 Like, why can’t you be happy in the moment?
0:39:08 You did this thing prior, you thought was great, like, why can’t you think it’s great?
0:39:14 And I think that can be true in some cases, but I actually think or I think that the trick
0:39:21 is, slash downside, is if you’re like only happy when you hit a goalpost and then you’re
0:39:23 moving them, like, you’ll never be happy.
0:39:28 If you actually just like the work, that’s what it doesn’t matter, and I think a lot
0:39:31 of things are more sustainable when you like the work, especially when you have a lot of
0:39:33 work to do.
0:39:37 My formula is progress equals happiness, which is that no matter where you are, sort of like
0:39:42 the why intercept doesn’t matter, the slope matters, and so wherever you’re at, if you
0:39:45 don’t feel a sense of progress in your life, you will feel unhappy, and then you’ll feel
0:39:46 even worse.
0:39:49 You’ll feel guilty for feeling unhappy because you’re like, “I guess I do have all these
0:39:51 good things in my life, but I still don’t feel this way.
0:39:52 I’m just fundamentally broken inside.
0:39:53 I’ll never be happy.”
0:39:54 Right.
0:39:55 Right.
0:39:56 When in actuality it’s just a sense of progress.
0:40:00 Even better, a sense of progress in a direction that you have set out intentionally that you
0:40:01 care about.
0:40:02 Yeah.
0:40:06 And I think that in that sense, moving the goalpost is great because you’re saying, “I
0:40:07 would like to continue making progress.
0:40:09 I enjoy progress so much.
0:40:10 Why would I stop my progress?
0:40:11 That stops my happiness.”
0:40:12 Yeah.
0:40:13 It’s a different way of looking at it.
0:40:18 Do you remember Deep Cut 10, 12 years ago, Jess, who’s that founder of Polyvore at the
0:40:21 time now at Sequoia wrote a blog post about founder psychology?
0:40:22 No.
0:40:23 What did it say?
0:40:27 It was basically like, “Why are founders always unhappy?”
0:40:31 And she’s like, “Especially when their companies go like this and it was a line up into the
0:40:32 right.”
0:40:41 And she’s like, “Because if you zoom in on the graph, it doesn’t look like a 45-degree
0:40:42 angle.
0:40:45 It looks like a roller coaster that is going slightly higher.”
0:40:46 Right.
0:40:50 And it looks like the roller coaster along the way and like, you know, again, even when
0:40:55 you zoom out and you’ve got this lovely 45-degree line, the downs hurt every time.
0:40:56 Right.
0:40:57 Yeah.
0:40:58 It’s the peak to trough that you feel.
0:40:59 Yeah, yeah, it’s that.
0:41:02 You don’t really even recognize that you’ve gotten higher progressively each time.
0:41:04 You also have another one, which is high standards are bad.
0:41:08 You think that in generally, you said people don’t say this, but they imply it in different
0:41:11 ways that, you know, don’t have such high standards.
0:41:12 Right.
0:41:15 What is, what’s the situation where that’s come up for you or you’ve felt that?
0:41:20 I think a lot of Vanta stuff and I think within the company and then with, you know,
0:41:24 kind of partners or folks outside and, I mean, some of the feedback we get that like, I kind
0:41:29 of, I don’t know, appreciate more than anything else is like, people care, people respond
0:41:34 super quickly, like, you know, we’re getting something might have gone wrong, but the person
0:41:37 tries really hard to fix it, right.
0:41:43 And I think those things definitely don’t happen everywhere by accident.
0:41:49 It’s not like I had, I mean, hopefully a small role in it, but I think when people join,
0:41:53 there’s a little bit of like, Oh, the bar is here at Vanta.
0:41:54 Like kind of scary.
0:41:55 Did I join the right place?
0:41:56 Like what’s going on?
0:41:57 What’s an example of that?
0:41:59 Where would somebody feel that?
0:42:04 A couple of places, but I guess in go to market or expectation, their own quota around attainment
0:42:07 on that they’re way off industry.
0:42:08 They’re way higher.
0:42:13 And I think if you just, if one just hears them in a vacuum, they’re sort of like, what
0:42:14 is what?
0:42:17 Like, why would I, why would I sign up for that?
0:42:20 Then they join and it’s like, Oh, cause you’re surrounded by people who are like into what
0:42:23 they do, getting better every day, want to get better every day, care a lot.
0:42:26 And that sort of environment can be like really infectious.
0:42:30 I’m curious, did you ever read this leaked production document from Mr. Beast?
0:42:31 You ever take a look at that?
0:42:33 Did you see that going around like a few weeks ago?
0:42:34 I know.
0:42:40 You know, so like right around the same time that Paul Graham put founder mode out there
0:42:42 and I’m like, Oh founder mode, like, but wait, what is it exactly?
0:42:48 And like, it was like, I think yes, but what part of a lawsuit Mr. Beast, like the internal
0:42:52 doc he wrote for his production team leaked, a big part, like we’ve gotten to know him
0:42:55 and become, you know, pretty friendly with Jimmy over time.
0:42:59 And it’s just done, like the number one thing you go hang out with Jimmy for a couple days,
0:43:04 like you walk away and you’re like, Oh, he, that’s what people, that’s what it means when
0:43:08 people say, you know, Steve Jobs used to have this reality distortion field.
0:43:12 And it’s, and literally he, he, his company is based in like a tiny town in North Carolina.
0:43:14 So like, he gets people to move there.
0:43:18 And then once you’re there, you’re in his bubble and in his bubble, the expectations
0:43:23 of what work is about what success is, about what we’re able to do, about the timelines
0:43:27 we do them on, about what it means when something says no, not possible.
0:43:30 And he’s like, one of his things is like, push past the no, he’s like, you know, you
0:43:34 have to be able to push past the no, you don’t always have to get it to be a yes.
0:43:38 And like, if you just come back and you said, Oh, we, you know, we asked for the permit
0:43:42 and they said it’s going to take six months and he like, that can’t be the end of the
0:43:43 story.
0:43:47 And we saw it on every little thing, like for example, we wanted to play basketball the
0:43:48 next day.
0:43:50 It was midnight and somebody was like, Oh man, I can’t wait till tomorrow.
0:43:51 Like, I just want to play.
0:43:53 And he goes, well, why do we have to wait?
0:43:54 I was midnight.
0:43:55 Jamie, what are you going to do?
0:43:57 He’s like, I’m sure there’s a gym around here somewhere.
0:43:58 Let’s go.
0:43:59 Let’s go find one.
0:44:00 And we’re like, yeah, but they’re going to be locked.
0:44:01 It’s midnight.
0:44:02 Like schools aren’t going to be open.
0:44:03 He’s called the athletic directors.
0:44:06 He’s like, just call, call all of them right now in the county.
0:44:09 It’ll take us 20 minutes and offer any of them a thousand bucks, see if they’ll come
0:44:10 open it.
0:44:13 And like, part of it was like, Oh, he just throws money at every problem, but actually
0:44:14 it’s not about throwing money at it.
0:44:18 It’s, everybody else would immediately just default to like, this is not possible, not
0:44:23 feasible, not, not going to be doable, whereas his default assumption on any given thing is
0:44:24 like, why not?
0:44:25 Of course we could do that.
0:44:26 It’s just a matter of deciding.
0:44:27 If we wanted it, we’ll do it.
0:44:28 If we don’t, we won’t.
0:44:29 But that’s it.
0:44:33 We’ll be that time after time after time hanging out with them on big things, like, you know,
0:44:36 the videos that they’re going to go shoot, but the small things.
0:44:37 And it’s just a different gear.
0:44:40 It’s like, Oh, your gear is like, my, my stick shift only goes to six.
0:44:41 Yours goes to nine.
0:44:42 Okay.
0:44:44 If I’m going to hang out with you, I now need to decide like how I’m going to get to eight
0:44:47 or nine because otherwise I’ll just be sticking out.
0:44:48 This won’t be the right place for me.
0:44:49 Yeah.
0:44:50 It totally.
0:44:55 And I think there’s a, I mean, I think also if you like experience that and you’re like,
0:44:56 you know what?
0:44:57 I’m going with six.
0:44:58 Right.
0:44:59 Totally reasonable decision.
0:45:03 But not that, you know, arguably maybe a better decision in some cases, like totally fine.
0:45:09 But the, the like, there might be, there might be a nine for any given thing.
0:45:11 I think of the helpful mindset.
0:45:14 You also raised a bunch of money late.
0:45:19 So you didn’t raise early on, you got to 10 million in ARR before you went and raised
0:45:20 your series A.
0:45:21 Yeah.
0:45:25 I’m not so curious about as to why you did that because I’m guessing the answer is pretty
0:45:27 simple, which is like, we didn’t necessarily need it.
0:45:29 We just stayed focused on selling the product.
0:45:31 That was working.
0:45:32 But more so when you went to go do it.
0:45:33 What was that experience like?
0:45:34 Oh, it was really fun.
0:45:35 Yeah.
0:45:36 It was great.
0:45:38 It was really funny.
0:45:44 So people or VCs in San Francisco broadly, like knew we were doing well because of kind
0:45:48 of the slack channel chatter or like advantage come up, but they sort of didn’t know how
0:45:49 well.
0:45:50 And so there was one pitch meeting.
0:45:51 I remember they.
0:45:52 And sorry, you kept it low key, right?
0:45:53 Yeah.
0:45:57 I kept it low key on purpose because basically we were like, we have this great idea and everyone
0:46:02 else thinks the can even like spell what we’re working on, think it, you know, has case and
0:46:04 to do with things on your feet.
0:46:07 And I would rather they not know, because then somebody’s going to start knocking soft
0:46:08 and copying.
0:46:10 But anyway, very smart VC.
0:46:12 Very good at his job.
0:46:18 Like go and pitch and I start walking through the slides and I get to the ARR ramp chart
0:46:23 that, you know, 10 at the end of it basically and his jaw just dropped and he was like clearly
0:46:24 speechless.
0:46:28 And he’s looking at it and he’s like, I thought you were at like two and a half.
0:46:33 And you’re like, no, that was, you know, 10 anyways, like keep going.
0:46:36 And at the end, it was sort of like, we’re like not going to like, we missed it.
0:46:38 Like, we’re not going to be able to do this.
0:46:41 I can like try to introduce you to someone else, but like, you know, it was fun, like,
0:46:45 you know, there were other people, but it was this kind of interesting pitch experience.
0:46:49 And then basically I go into a meeting with another VC, he’s very good at his job.
0:46:54 And he’s like, you know what, thought you were at 9.4 because I’d like taken your Twitter
0:46:55 chart and backed it out.
0:46:56 I did the same, actually.
0:46:57 And like counted the pixels.
0:46:58 I did the proportions.
0:46:59 She said 10.
0:47:00 So this is 10.
0:47:01 Yeah.
0:47:02 Where was she a year ago?
0:47:03 Yeah.
0:47:04 2.7 or whatever.
0:47:05 Totally.
0:47:06 He had basically done that.
0:47:07 And that was also, you’re like, hell, this is great.
0:47:08 It’s so good at your job.
0:47:09 So fun.
0:47:10 Is that who you end up going with?
0:47:11 Or no?
0:47:12 No.
0:47:13 You’re great.
0:47:14 But Sequoia’s gone.
0:47:26 But I think actually it was, it’s all the goalpost stuff and I’m not very good at celebrating,
0:47:30 but it was a moment where I like took a, I mean, I’ll be like a week and I was like,
0:47:35 no, I am going to like tell this story and what we’ve done and like, I’m deeply proud
0:47:36 of it.
0:47:40 And I would have told you that, but now I like feel overwhelmingly proud of it, right?
0:47:42 And like, here’s how the pizzas fit together.
0:47:43 Here’s how they will fit together.
0:47:44 And I believe it.
0:47:51 And so that was just, then it became like, I still kind of hate fundraising, but it
0:47:56 was talking about something I believed in, just fun, right?
0:47:58 Eric told me that he thinks you’re great at negotiating.
0:48:04 You said, you said, that’s surprising to you, but he was not, he was not wishy-washy
0:48:05 about it.
0:48:08 He’s like, she’s incredible at negotiating, one of the best I’ve ever been around, ask
0:48:09 her how or why she does it.
0:48:10 So no pressure.
0:48:11 Yeah.
0:48:12 No, it’s really surprising.
0:48:17 I think, if I’m confident in it, I’m actually confident in it, and then we’ll just stand
0:48:22 and like, not blink, not swerve if we’re playing chicken, won’t eat the marshmallow.
0:48:24 It’s like, I got it.
0:48:26 Like, let me know when you want these terms.
0:48:28 I’m happy to sit here and wait.
0:48:30 And actually truly, I’m like happy to sit there and wait at that point.
0:48:31 So I think it’s just a lot of that.
0:48:33 It’s like, I won’t, I believe it.
0:48:34 I won’t flinch.
0:48:35 Cool.
0:48:36 Well, thank you for doing this.
0:48:37 This has been amazing.
0:48:39 Where should people find you?
0:48:40 Find Vanta.
0:48:41 Maybe you give it a shout.
0:48:42 Yeah.
0:48:43 Thank you for doing this.
0:48:44 Thank you so much.
0:48:45 Awesome.
0:48:46 Thank you for doing this.
0:48:47 Thank you so much.
0:48:48 I feel like I can rule the world.
0:48:49 I know I could be what I want to.
0:48:50 I put my all in it like no days on.
0:48:51 On the road, let’s travel, never looking back.
0:48:52 Why?
0:48:53 Why?
0:48:53 Why?
0:49:02 Why?
0:49:03 Why?
0:49:05 Why?
0:49:07 Why?
0:49:09 Why?
0:49:11 Why?
0:49:12 Why?
0:49:13 Why?
0:49:14 Why?
0:49:15 Why?
0:49:16 Why?