Building the Leading Company in a Competitive Space | Christina Cacioppo, CEO of Vanta | Ep. 17

Christina Cacioppo 0:00 No, you just have to, like, Stockholm syndrome yourself-

Jack Altman 0:01 Yeah

Christina Cacioppo 0:01 -into being like, "Well, I used to be someone who liked to build products."

Jack Altman 0:04 Yeah, yeah.

Christina Cacioppo 0:04 "But now I love building teams. And whether or not I identified as that person two years ago-"

Jack Altman 0:08 Yeah, now that's me.

Christina Cacioppo 0:08 "-doesn't matter. Now that's me," and I believe it, you know? And then, like, when it changes, you're like, "Now I'm this person."

Jack Altman 0:13 Yeah. Yeah.

Christina Cacioppo 0:13 "I love HR policy," [chuckles]

Jack Altman 0:15 [chuckles] Yeah.

Christina Cacioppo 0:16 You know? 'Cause that's what the company needs right now. [upbeat music]

Jack Altman 0:19 All right, I'm here with Christina from Vanta, and very excited for this conversation. Thanks for doing this with me.

Christina Cacioppo 0:23 Thanks so much for having me.

Jack Altman 0:24 Okay,

Jack Altman 0:25 so what I want to start with is we are in a moment with AI where I would say markets are probably as promising, but also as competitive as they've ever been. There's a lot of ideas that seem very greenfield, and the result of that is there's tons of startups going at them, and so I think a very, very common founder experience today is you build a thing that makes a lot of sense, and you look around you and there's thirteen other companies also building something that makes a lot of sense. You've operated in a really competitive market for a really long time, and so I thought something founders could learn from you about would be operating in a competitive market, so I want to start there. I guess the first place I wanted to go with it is the mentality, I think, that you've learned over the years that it takes to succeed. So can you talk a little bit about what's the mindset that you've gotten yourself to over the years?

Christina Cacioppo 1:10 Yeah, for sure, and a bit of, like, very short version of the history, which is Vanta started in twenty eighteen. We were the first person who did what we did. We had about two years where our competitors were accountants and consultants, and when we were selling to founders and engineers, that was wonderful. "Would you like software or would you like an accountant?"

Jack Altman 1:26 Right.

Christina Cacioppo 1:26 And then... and tried to kind of keep it quiet about how well we were doing. Word got out, and then in twenty twenty, when everyone was at home bored, lots of people started Vanta competitors.

Jack Altman 1:34 You did try to keep it quiet for a while, though, right?

Christina Cacioppo 1:36 We did, yes.

Jack Altman 1:36 Yeah.

Christina Cacioppo 1:37 And some of it actually was like, "We know that this is really good, and we know people will knock it off, so how far can we run?"

Jack Altman 1:42 And your mindset was basically just, like, "Let's get as much-

Christina Cacioppo 1:45 Much

Jack Altman 1:45 ... traction as possible before people think that this is a good idea."

Christina Cacioppo 1:48 Yes, 'cause people thought it was a terrible idea.

Jack Altman 1:49 Mm-hmm.

Christina Cacioppo 1:50 No startup got SOC 2s. No one knew what it... No one could spell it. It was just like, "Why are you, like, seemingly nice people working on compliance? Like, what's... Like, do you need some help?" Like [chuckles]

Jack Altman 1:58 And how did you know it was good? How did you have the confidence to know it was good enough that you should keep it a secret?

Christina Cacioppo 2:02 Because when you talk to peop- when you talk to founders who had this problem, they were like: "I will pay you any amount of money, and I will crawl through any amount of muck for this."

Jack Altman 2:09 Wow.

Christina Cacioppo 2:10 It's like: "I really want this thing, and I can't get it, and if you can get me there, I am all here for whatever you put me through."

Jack Altman 2:17 Were you getting customers with, like, a janky product?

Christina Cacioppo 2:19 A hundred percent.

Jack Altman 2:20 Yeah.

Christina Cacioppo 2:20 During YC, a YC company that bought Vanta called it the brutalist white website. [chuckles]

Jack Altman 2:24 [chuckles]

Christina Cacioppo 2:24 Like, yeah. [chuckles]

Jack Altman 2:25 That's nice.

Christina Cacioppo 2:26 Yeah, you know, that was, that was... The brutalist white website sucked in a million ways, except it got people to their outcome.

Jack Altman 2:33 I guess you also had a very good "why now," right?

Christina Cacioppo 2:35 Yeah.

Jack Altman 2:35 Like, there, like, a thing really happened.

Christina Cacioppo 2:37 Kind of, or, like, yes.

Jack Altman 2:38 Or did that just seem that way?

Christina Cacioppo 2:39 It just seemed that way.

Jack Altman 2:40 Oh.

Christina Cacioppo 2:40 Like, the why now existed in twenty sixteen and twenty fourteen. I think, like, why was it eighteen? And I think it was 'cause generally, if you said compliance to an engineer, they ran screaming from the room.

Jack Altman 2:50 So what was the first year it could have happened?

Christina Cacioppo 2:52 Fourteen, probably.

Jack Altman 2:53 Fourteen.

Christina Cacioppo 2:53 Thirteen, fourteen.

Jack Altman 2:54 Okay.

Christina Cacioppo 2:54 Yeah.

Jack Altman 2:54 So it was a reasonable thing, but it was like-

Christina Cacioppo 2:56 But I couldn't give you a-

Jack Altman 2:57 A startup could have done it for a few years.

Christina Cacioppo 2:59 Yeah.

Jack Altman 2:59 Okay.

Christina Cacioppo 2:59 And so that's actually... I used to love the why now question, especially with that USB. You're like, "Oh, it's so intellectual," and like-

Jack Altman 3:04 Well, I didn't know that there was that gap in time between-

Christina Cacioppo 3:06 But now with Vanta, you're like, "Yeah, yeah, yeah.

Jack Altman 3:07 Yeah, yeah.

Christina Cacioppo 3:08 Like, I only have like, one why now."

Jack Altman 3:08 I thought Vanta was the first one take- which I guess you were the first one to take advantage of it.

Christina Cacioppo 3:12 We were the first one, but, like-

Jack Altman 3:13 But somebody else could have.

Christina Cacioppo 3:14 Someone could have.

Jack Altman 3:15 Yep.

Christina Cacioppo 3:15 Yeah.

Jack Altman 3:15 Okay.

Christina Cacioppo 3:15 There were a couple really manual solutions, but I think it was like lawyers looked at the problem, compliance people looked at the problem, and they s- they solved it in just a different way than an engineer.

Jack Altman 3:24 Yeah.

Christina Cacioppo 3:25 But, like, we weren't particularly smart. You know, it's like anyone could have figured that part out.

Christina Cacioppo 3:29 They just didn't.

Jack Altman 3:29 Okay, so you, you-

Christina Cacioppo 3:30 Yeah

Jack Altman 3:30 ... stayed secretive as long as you could.

Christina Cacioppo 3:31 Yeah.

Jack Altman 3:31 But then at some point, you didn't, you weren't secretive.

Christina Cacioppo 3:33 Yeah. Well, and word kind of got out, and so, and then we got this, like, host of knockoffs, and, you know, I think we went through, like, "Oh, well, they're just knocking off," or, like, "Oh, they took screenshots of Vanta and sent them to a dev shop in Mexico and got the product back," and then said, "Vanta took two years to build this, and we built it in two months-

Jack Altman 3:49 Uh-huh

Christina Cacioppo 3:49 ... and, like, they suck, and we're awesome."

Jack Altman 3:51 Is that how they said it to you?

Christina Cacioppo 3:52 Yes, yeah, literally in that-

Jack Altman 3:53 That was their voice.

Christina Cacioppo 3:53 Yes.

Jack Altman 3:53 Yeah.

Christina Cacioppo 3:54 Very surfer bro.

Jack Altman 3:54 Uh-huh.

Christina Cacioppo 3:55 You know, we, like, went through the phase of, like, "Well, that won't work," or, "That's not fair," like... And I think the thing, it, you know, you learn is, like, all's fair in love and capitalism.

Jack Altman 4:05 Mm-hmm.

Christina Cacioppo 4:06 And it doesn't... You know, no one cares, and, like, customer, like, customers are trying to solve the problem.

Jack Altman 4:12 Yep.

Christina Cacioppo 4:12 And, like, they don't care if you're first. They care if you're the best thing today.

Jack Altman 4:15 Yep.

Christina Cacioppo 4:16 They don't care if, you know, you were secret shopped, and someone took screenshots and, like, ripped everything off. There's no referees in capitalism.

Jack Altman 4:23 Yeah.

Christina Cacioppo 4:24 Um, and you kind of want there to be one, but, like, there's not.

Jack Altman 4:26 There's not.

Christina Cacioppo 4:27 And I think you've got to stop searching for one, and-

Jack Altman 4:30 Did you have a thing switch for you?

Christina Cacioppo 4:31 Yeah.

Jack Altman 4:31 Like, were you at one point looking for a referee, and then you decided to stop?

Christina Cacioppo 4:34 Kind of, yes, and then you're like, "There, like, what am I..." You know, like, even, like, "If I had a magic wand, what would I con? Like, what would the referee..." And you're like, "I don't know," you know?

Jack Altman 4:42 Right.

Christina Cacioppo 4:42 Um, I think you see, you see investors fund these. Like, investors don't care.

Jack Altman 4:46 Yeah.

Christina Cacioppo 4:46 And you, like, kind of take it personally, and then you're like, "You know, it's, like, not. It's capitalism."

Jack Altman 4:50 Yep.

Christina Cacioppo 4:50 "Like, it's not personal."

Jack Altman 4:51 Yep.

Christina Cacioppo 4:52 And so I think the, the switch was eventually it's like, cool, we started this thing, but again, no one cares. I'm also kind of trying to de-emphasize it. I mean, it's important internally, but it's also not, or not in a, like, rest on your laurels way.

Jack Altman 5:02 Yeah.

Christina Cacioppo 5:02 Like, I think a lot of it, why I do and a lot of us like software is 'cause it's so fast-moving.

Jack Altman 5:07 Mm-hmm.

Christina Cacioppo 5:07 Blessed and cursed, and you are, like, only as good as the last thing you shipped.

Jack Altman 5:10 Yep.

Christina Cacioppo 5:10 And so it's like, okay, cool, what have you shipped for me lately?

Jack Altman 5:12 Yeah.

Christina Cacioppo 5:13 And, like, that's how customers think, and that is great and terrible but, like, also reality, and so you just gotta go with that.

Jack Altman 5:19 Yeah.

Jack Altman 5:20 What else from a mindset, you know, perspective did you end up building over time, besides, like, all's fair in love and capitalism-

Christina Cacioppo 5:26 Yep

Jack Altman 5:26 ... which I think is, like, a very, uh, that is, like, hard, hard-earned wisdom, but what else came to you over time?

Christina Cacioppo 5:33 Shipping velocity, uh, 'cause I think also, you know, then the Vanta, and even the Vanta of, like, a pre-competitive era, we, like, tried to get stuff right the first time, and so we'd write these long specs and do all this work and then, like, take a long time to ship something, and then it was wrong, and not, you know, through anyone's fault. It's just usually the first thing you put in front of a customer is, in fact, wrong, but we would, like, had spent six months on that-

Jack Altman 5:55 Right

Christina Cacioppo 5:56 ... and then we get this kind of negative feedback, and then, so, and we're just, like, very demoralized.... and then customer's like, "What have you shipped for me lately?" Like, nothing.

Jack Altman 6:03 Yeah.

Christina Cacioppo 6:04 Right? And so trying to get to, like, the frame, and I feel this way in my career, too, it's like I very rarely, if ever, ship the right thing the first time, but I can usually ship the right thing by, like, the fourth time.

Jack Altman 6:14 Yep.

Christina Cacioppo 6:15 And so in a team, it's like, how do you minimize the time between, you know-

Jack Altman 6:19 Like-

Christina Cacioppo 6:19 ... the zero and then the fourth time? [chuckles]

Jack Altman 6:20 How quickly can we get to V4?

Christina Cacioppo 6:22 Exactly.

Jack Altman 6:23 Yeah.

Christina Cacioppo 6:23 And like, V4 should be right, and I'll hold you to that, but V1, like, V1 does not have to be right, and like, trying to switch to that mindset-

Jack Altman 6:30 Yeah

Christina Cacioppo 6:30 ... 'cause I think we had a lot of people who are, you know, like, good students, and done well in school, and wanna get it right on the test, and get it right the first time, and feel bad. And you're like, "No, no, no." Like, that's the mental model of school, but actually not to real life.

Jack Altman 6:40 Totally.

Christina Cacioppo 6:41 And trying to, like, flip that, too.

Jack Altman 6:43 Competition is one of the, like, more, um, psychologically vexing parts of a startup.

Christina Cacioppo 6:47 Yeah.

Jack Altman 6:48 Do you try to minimize how much you think about it or how much your team thinks about it? Like, what's the... What have you tried to cultivate for yourself, your exec team, your broader team, about competition?

Christina Cacioppo 7:01 I think there is, and this works kind of sometimes well and sometimes not, but I think for me, what I- when I'm at my best, what I try to do is, like, if a competitor is do- if the competitor is just copying, like, fine. But also there's a little bit of, like, how can we use that to our advantage? And we have in some ways, where we're like, "We're gonna call this new field this, and like, everyone's gonna call it!" And like, have we created a category now, right? [chuckles] Like, there's, there's parts you can kind of weaponize for yourself.

Jack Altman 7:24 Yeah. Yeah.

Christina Cacioppo 7:24 The other part is if do something different-

Jack Altman 7:26 Yep

Christina Cacioppo 7:26 ... why? And I think it's trying to start from the, like, assume they're smart-

Jack Altman 7:29 Mm-hmm

Christina Cacioppo 7:30 ... not, like, assume they're idiots.

Jack Altman 7:31 Yep.

Christina Cacioppo 7:32 And be like, "What do they know that I don't?" And try to figure that out. And again, maybe you conclude they know nothing you don't and they're idiots, but like, I think it is a u- always a useful thought exercise, even if you've dismissed them the last ten times or something like this-

Jack Altman 7:45 Yeah. Have you had it go the other way, where you've ended up cloning something from a competitor? 'Cause, like, yeah, they figured something out good.

Christina Cacioppo 7:49 Yeah, actually, um, there was a bunch of... One of our com- early competitors was really good at talking to our customers and finding out the parts of the product they didn't like and fix them.

Jack Altman 7:57 Mm.

Christina Cacioppo 7:57 It was particularly brutal, honestly, 'cause it was like, "Oh, yeah, they just listened to our customers better than we did."

Jack Altman 8:02 Uh-huh.

Christina Cacioppo 8:03 And so that, we were like, "Okay, like, that needs, that needs to stop-

Jack Altman 8:06 Yeah

Christina Cacioppo 8:06 ... right now." [chuckles]

Jack Altman 8:07 Yeah, totally.

Christina Cacioppo 8:08 Yeah.

Jack Altman 8:08 Yeah.

Jack Altman 8:09 Have you learned anything about how to do, like, the go-to-market side in a competitive market, whether it's, like, the way you, you know, position at the top of the funnel... I mean, like, you had... I think you've been running the, like, compliance that doesn't-

Christina Cacioppo 8:22 Yeah

Jack Altman 8:22 ... talk too much billboards for a long time. That's still, like, the best billboard I've ever seen.

Christina Cacioppo 8:25 It's after twenty twenty-one-

Jack Altman 8:27 Yeah

Christina Cacioppo 8:27 ... was its debut.

Jack Altman 8:28 It's crazy.

Christina Cacioppo 8:28 Yeah.

Jack Altman 8:28 You keep it going.

Christina Cacioppo 8:29 Yeah.

Jack Altman 8:30 Yeah.

Christina Cacioppo 8:30 That billboard's locked up for-

Jack Altman 8:31 Ten more years.

Christina Cacioppo 8:32 Like, kind of, actually. [chuckles]

Jack Altman 8:33 I love that.

Christina Cacioppo 8:33 Yes. [chuckles]

Jack Altman 8:34 But, like, what have you learned in sort of, like, the way that you structure your go-to-market when you're... I mean, most markets are really competitive, but, like, what have you learned?

Christina Cacioppo 8:40 Yeah. I think one bit is, like, man, AE confidence is so real, and not as rational as, like, a EPD person, like a engineer or a PM would imagine.

Jack Altman 8:50 Yeah.

Christina Cacioppo 8:51 And that works on the way up, and it works on the way down.

Jack Altman 8:53 Uh-huh.

Christina Cacioppo 8:53 When the team is starting to lose confidence, like, you've gotta go fast, and you can't just go in with logic, and I think we messed that up for a while.

Jack Altman 9:00 Mm.

Christina Cacioppo 9:01 Um, and it works on the way up, too, and but then it kind of becomes this, like, how do you build confidence amongst your salespeople?

Jack Altman 9:07 How do you build it?

Christina Cacioppo 9:08 What we did, and this is all credit to our CRO, Stevie, was one of the- one of our issues with early competitors was they were actually so good at, like, secret shopping Vanta and, like, maybe exfiltrating... You know, like, they just, like, knew everything, and we knew very little.

Jack Altman 9:23 Mm.

Christina Cacioppo 9:23 And I think we were also, like, very Midwestern, like, nice, like, "Oh, but we're nice, and isn't it?" You know, and, like, not, not good at competitive intel. [chuckles]

Jack Altman 9:29 Yeah.

Christina Cacioppo 9:29 And so the way we solved that was we put one or two people on every competitive deal, and they just, like, listened to all the call, or, like, they were in all the calls. They talked to all the customers. They talked to, like, rip customers in both directions, and they just got smart-

Jack Altman 9:44 Mm

Christina Cacioppo 9:44 ... about what was going on.

Jack Altman 9:46 Yep.

Christina Cacioppo 9:47 And they figured out the talking points and the weak points and all of that, and then they got confident in winning, and it was one or two people, and then we started adding them to everybody else's calls, and then, like, AEs would be like, "Oh, I want that person to come join."

Jack Altman 9:58 To show the confidence, yeah.

Christina Cacioppo 9:59 Exactly. And, like, when I add them, I win more, so, like, definitely want them in.

Jack Altman 10:03 Yep.

Christina Cacioppo 10:04 And then that, like, sort of osmost out.

Jack Altman 10:06 That's brilliant.

Christina Cacioppo 10:06 There's also honestly probably something there, is we tried to do all this enablement with, like, enabling people, and PMMs, and me, and-

Jack Altman 10:12 Mm

Christina Cacioppo 10:12 ... PMs. None of it works. Like, I mean, it works, and everyone tries really hard-

Jack Altman 10:17 Yep

Christina Cacioppo 10:17 ... but, like, salespeople learn from salespeople, and everyone else is, you know, not as good. [chuckles]

Jack Altman 10:21 Yeah.

Christina Cacioppo 10:21 Doesn't matter, like, who you are or what you're trying to do.

Jack Altman 10:23 Yeah, totally.

Jack Altman 10:25 Um, I wanna go over to fundraising. I guess you started fundraising at your seed in, when was it? Two thousand eighteen?

Christina Cacioppo 10:32 Mm-hmm.

Jack Altman 10:32 Is that right?

Christina Cacioppo 10:32 April '18.

Jack Altman 10:33 April '18. You then, I think, if I recall, had, like, a lot of investors who wanted to talk to you over a period of time between then and your A.

Christina Cacioppo 10:40 Yes.

Jack Altman 10:41 Can you just talk about, like, some of the stuff you did? I know we've talked about this before-

Christina Cacioppo 10:44 Yeah, yeah

Jack Altman 10:44 ... but, like, what, can you talk about in that period, how you made most use of that time?

Christina Cacioppo 10:48 Yeah, so I think, so for the seed, what we did was only took money from seed funds. The thinking was, or, like, don't take money from anyone who will write an A check, because we did the, like, post-YC, you know, raise your seed round in six days-

Jack Altman 11:00 Yep

Christina Cacioppo 11:01 ... crazy thing, and didn't wanna choose a board member. And so, like, that just felt silly. Board members are, like, harder to get rid of than-

Jack Altman 11:07 Yep

Christina Cacioppo 11:07 ... you know, execs, co-founders, right? Like, choose, be, be thoughtful about that decision. And then I did a... I can't remember who told me to do this. Raised the seed round, then went around to all the A firms, and we're like, "Hi, just interesting vendor. We just raised. No opportunity for you here. Just wanna say hi," and, like, put the first, like, put the first dot on the map.

Jack Altman 11:25 Like, right after the round?

Christina Cacioppo 11:26 Right after the round.

Jack Altman 11:27 Like, within weeks kind of thing?

Christina Cacioppo 11:28 The one week.

Jack Altman 11:29 Wow.

Christina Cacioppo 11:29 It was like, schedule all of them, but to schedule them after it's done.

Jack Altman 11:32 Wow.

Christina Cacioppo 11:32 Yeah, um, and so just like, "Just saying hi."

Jack Altman 11:34 Someone gave you advice to do that?

Christina Cacioppo 11:35 Yeah, and it's like putting, putting myself on the map, you know, nothing for you now, but, like, here you go.

Jack Altman 11:40 I love that. It also creates a very low-stakes conversation, where nobody is thinking, like, that they can ask you about certain... Like, you just can control that conversation so easily-

Christina Cacioppo 11:48 Yes

Jack Altman 11:48 ... I bet.

Christina Cacioppo 11:48 Yes.

Jack Altman 11:49 Yeah.

Christina Cacioppo 11:49 So did that, and then it was like, I obviously, there was this moment of, like, "Shit, we just, like, raised three million dollars to do all this stuff, and we have, you know, two people sitting on a couch." Like, [chuckles] "We gotta, gotta, we gotta get, we gotta get hopping."

Jack Altman 12:00 Yep.

Christina Cacioppo 12:01 So there was some moment of just that, and then at some point-... six months later, you're like, "Okay, this is working." Like, this is different. Vanta feels different than literally everything else I've worked on in my career.

Jack Altman 12:11 Mm-hmm.

Christina Cacioppo 12:12 It is a true, like, pulling- like, the market is pulling something out.

Jack Altman 12:15 Mm-hmm.

Christina Cacioppo 12:16 There's a million things wrong and a million things going on, but, like, there's something here. And then did not really talk to VCs. I think what started happening was there was, like, some amount of word of mouth among San Francisco founders about, like, "Hey, if you want to SOC 2, there's this Vanta thing." We had this sort of call response of, like, SOC 2 Vanta going. It would start to come up with these companies' VCs.

Jack Altman 12:38 Mm.

Christina Cacioppo 12:38 They would start to talk to us, and look, it was like half I was playing a game, and half was actually really busy, but I generally reply and be like: "Look, I am just too busy-

Jack Altman 12:47 Yeah

Christina Cacioppo 12:47 ... fielding customer calls."

Jack Altman 12:48 Yeah.

Christina Cacioppo 12:49 'Cause like, I was. "Like, I don't have time to meet with you, but it sounds like you know, you know, this founder at this company. You can go talk to them."

Jack Altman 12:58 Yeah.

Christina Cacioppo 12:59 "And, like, look-

Jack Altman 13:00 An existing customer of yours.

Christina Cacioppo 13:01 "An existing customer."

Jack Altman 13:02 Yeah.

Christina Cacioppo 13:02 "And look, the thing, you know, I'm trying to do is grow the business, and so if you have referrals for me, I mean, of course I'll take them. But, like, then go talk to them. Talk to them about the sales process, if they'd buy, if they don't buy, talk to them about the process."

Jack Altman 13:15 Right.

Christina Cacioppo 13:15 "Like, that is better diligence and information than I could ever give you."

Jack Altman 13:18 Yeah, if you want to see if Vanta's good, go try to send us a customer, see if they close-

Christina Cacioppo 13:21 And see if it works

Jack Altman 13:22 ... and then see if they're happy.

Christina Cacioppo 13:22 Yeah, and it's like that is better than anything I would tell you.

Jack Altman 13:24 And that happened?

Christina Cacioppo 13:25 Amazingly so. [chuckles] That worked very well.

Jack Altman 13:28 Yeah.

Christina Cacioppo 13:28 You know, and I do think there was, like, a, a game, but I kind of call it a game because I'm a bit of like: "Oh, no, sorry, I'm so- I'm just too overwhelmed by like, you know, customers and dollars." So like-

Jack Altman 13:35 And there's an implied dynamic in there of, "If you want to get time with me, send me a lot of customers."

Christina Cacioppo 13:39 Yes.

Jack Altman 13:39 Yeah.

Christina Cacioppo 13:39 And it... And you have to kind of be careful to not sound like-

Jack Altman 13:41 Yeah, you can't say it

Christina Cacioppo 13:41 ... total jerk.

Jack Altman 13:42 Yeah.

Christina Cacioppo 13:42 Yeah, [chuckles] 'cause I think you can very easily go to jerk territory.

Jack Altman 13:45 Yes.

Christina Cacioppo 13:45 Or, like, especially if your thing isn't working.

Jack Altman 13:47 Right.

Christina Cacioppo 13:48 You know, it's like they send you a bunch of stuff, and like-

Jack Altman 13:49 Yeah. Well, part of why that thing works is because that's an incredibly confident dynamic-

Christina Cacioppo 13:54 Right

Jack Altman 13:54 ... for you to be running.

Christina Cacioppo 13:55 Yes.

Jack Altman 13:55 Yeah, which helps.

Christina Cacioppo 13:56 Which helps, and I think-

Jack Altman 13:57 Yeah

Christina Cacioppo 13:57 ... you know, I think one of my pieces of advice for founders is, investors are not people you should seek approval from. They want to back people who are confident in what they're doing-

Jack Altman 14:07 Yeah

Christina Cacioppo 14:08 ... not people who are seeking their approval.

Jack Altman 14:09 And it's really hard. There's a real dynamic where founders want investors' approval-

Christina Cacioppo 14:13 Yes, I-

Jack Altman 14:13 ... particularly early because-

Christina Cacioppo 14:15 Yeah

Jack Altman 14:15 ... I think, like, at least in my experience, it was like before I had real customer traction, you're like, well, at least investors, you know, think that this is worth backing.

Christina Cacioppo 14:22 Right.

Jack Altman 14:22 So that gives me something to hold onto.

Christina Cacioppo 14:24 Yes, and whereas I think... And I think I just, like, well, got lucky in lots of ways, but got lucky 'cause early in my career I worked for really good early-stage investors, and I kind of saw these pitches and be like, "Oh, no, this is not compelling." You want to back the person who, like, believes in where they're going, and that might change a million places, but can put one foot in front of the other-

Jack Altman 14:42 Yeah

Christina Cacioppo 14:42 ... and not look up and be like, "Is this right? Am I on the right trail?"

Jack Altman 14:45 Yep.

Christina Cacioppo 14:45 And so then I think it's like, okay, as a founder, how do you get that? And some people can just kind of manifest their confidence, which is great, and I'm very jealous of, and I've always [chuckles] been a like, need to figure it out and do it to get confident.

Jack Altman 14:56 Yeah.

Christina Cacioppo 14:56 But, like, it sort of doesn't matter. It's like as long as you are, you are confident in the way you get confident doing that, and that makes the founder, like, much more compelling to investors. But, you know, they should also just be, like, much more compelling to customers and, like, building said business.

Jack Altman 15:10 So what ended up happening at your Series A?

Christina Cacioppo 15:12 I-

Jack Altman 15:12 Or the round when you picked a board member, basically.

Christina Cacioppo 15:14 Yeah, so it was that one. So there was this whole... You know, had this whole framework on how we choose a board member and, like, did reference calls for people, and I had this spreadsheet. I remember I did some of them over the holidays, 'cause it was like customers weren't emailing, like, I just had time-

Jack Altman 15:28 Yeah

Christina Cacioppo 15:28 ... more time. And had this whole thing, and then literally ended up choosing an investor and board member who wasn't on the spreadsheet.

Jack Altman 15:35 Interesting.

Christina Cacioppo 15:35 Like, fell off the framework. [chuckles]

Jack Altman 15:36 How'd that happen?

Christina Cacioppo 15:37 I was not going to talk to Sequoia-

Jack Altman 15:39 Mm

Christina Cacioppo 15:40 ... because, I mean, they're great, all the things, um, but just actually in those like early days of like, "Hi, you know, I don't have anything to... You know, I might have something to talk about you later, but I'm like showing up today."

Jack Altman 15:50 Yep.

Christina Cacioppo 15:50 They were, like, very politely, entirely uninterested, and just like, "Nice girl, bad idea. Maybe she'll work at one of our companies one day," you know? [chuckles]

Jack Altman 15:59 Uh-huh.

Christina Cacioppo 15:59 And they were like... They didn't quite say that, but it was like, totally the vibe.

Jack Altman 16:01 That was the vibe.

Christina Cacioppo 16:02 Totally. Um-

Jack Altman 16:03 Were they sending you customers, or they weren't even-

Christina Cacioppo 16:05 No. [chuckles]

Jack Altman 16:05 They were not playing along on the back end?

Christina Cacioppo 16:07 No, zero. [chuckles] They were just like, "Wonder when that company's gonna die?"

Jack Altman 16:10 Like, nope. [chuckles]

Christina Cacioppo 16:10 [chuckles] Very politely, though.

Jack Altman 16:12 That's nice.

Christina Cacioppo 16:13 And so it was like, cool, like, I don't have to talk to you. You know, like, cool, great. Agree to disagree. I want to be in this, you don't, whatever. And then it was, uh, a kind of close friend to both of us who was like, "You're being an idiot. Just, you know, call Sequoia. What are you doing?" And so had another mutual friend introduce me to Andrew Reid, and, uh, he's great. I ended up going with him, and no regrets, but also no framework. [chuckles]

Jack Altman 16:33 Yeah.

Christina Cacioppo 16:33 Or, like, framework left by the wayside.

Jack Altman 16:35 Yeah. On

Jack Altman 16:36 this podcast, I've talked to a bunch of VCs about in what ways they think VCs might be helpful.

Christina Cacioppo 16:41 Uh.

Jack Altman 16:41 But I'd like to hear from you, in what ways you think VCs might be helpful, uh, to the extent that you think that they are.

Christina Cacioppo 16:47 Sometimes, some of them. I think VCs, I mean, at their best, like all of us, like, smart, motivated people who are good at their jobs. Their jobs are investing, their jobs are not operating. Like, the, like, that is a... Like, it sounds dumb and trite, but I think there's something deeply there. Like, they're probably not good at running companies, or if they are, and are now doing, like, they've now cho-

Jack Altman 17:07 They're not good at running your-

Christina Cacioppo 17:08 No, they've now chosen to do something else and, like, don't want to run your company. [chuckles]

Jack Altman 17:11 Right. Yeah.

Christina Cacioppo 17:11 You can explain this better than I can.

Jack Altman 17:13 It... Yeah, and they probably couldn't run your specific company anyway.

Christina Cacioppo 17:16 Right.

Jack Altman 17:16 Yeah.

Christina Cacioppo 17:16 And so when you're looking to them for like... Or, like, things they're probably not good at is, you know, how do you, like, hire your first salesperson? How do you compensate them when, like-

Jack Altman 17:25 Yeah

Christina Cacioppo 17:25 ... Chili Piper starts writing leads under a couch cushion, what do you do? Like, that is not VC stuff-

Jack Altman 17:30 Yeah

Christina Cacioppo 17:31 ... almost universally. Or if it is, I guess and you're not, like, super, super early stage or some special thing, like, something's probably off.

Jack Altman 17:39 Right. Well, they're probably capable of giving you an answer to that. It's actually, I would think, it's more like you probably shouldn't need to ba- there, you probably should have other vehicles to get that stuff.

Christina Cacioppo 17:47 Right.

Jack Altman 17:47 Yeah.

Christina Cacioppo 17:47 I think, um, recruiting support, especially in the early days.

Jack Altman 17:52 Yeah. When you say recruiting support, do you mean sending you candidates, or do you mean closing candidates?

Christina Cacioppo 17:57 I more mean closing candidates. There's some sending of candidates, but I do think that is, uh, like-

Jack Altman 18:01 Do you find the sending of candidates helpful, or do you think the closing of them is all about?

Christina Cacioppo 18:05 Tomato, tomato. Yeah.

Jack Altman 18:06 Yeah.

Christina Cacioppo 18:06 Yeah.

Jack Altman 18:06 Yeah.

Christina Cacioppo 18:07 I mean, like, there's some stuff there, and but I think in the early stages, and it's like Sequoia's model is like, "Okay, we'll send you candidates up until this point, and then we will basically cut you off."

Jack Altman 18:14 Did you get candidates from that?... [sighs] I mean, did you get hires from that?

Christina Cacioppo 18:19 Very rarely.

Jack Altman 18:20 Yeah.

Christina Cacioppo 18:20 Yeah.

Jack Altman 18:21 Yeah.

Christina Cacioppo 18:21 I also think in general, like, those are hard because the candidate you're getting from that lead flow is also going to 14 other companies.

Jack Altman 18:28 Mm-hmm.

Christina Cacioppo 18:29 And then, so then you're like, "Okay, you were, like, one in the, like, cohort, but, like, how are you differentiated?"

Jack Altman 18:33 Yeah.

Christina Cacioppo 18:33 "Do they ca-," you know, like, there's j- those are hard candidates to close.

Jack Altman 18:35 How does the closing play out? So, like, what's the way that... 'Cause I, that's how I most, you know, poignantly, I would say, use my board.

Christina Cacioppo 18:42 Mm-hmm.

Jack Altman 18:42 I'm curious what that played out like for you.

Christina Cacioppo 18:44 Yeah, so I think in the early days, there is a bit of the, like, the brand and the, like, "Oh, you know, here you have person from Sequoia, whose, you know, legendary firm-

Jack Altman 18:52 Yeah

Christina Cacioppo 18:52 ... from, you know, founding the IPO," and whatever, you know? [chuckles] And like, "Let me tell you why Vanta is going to be the next thing we put on the wall."

Jack Altman 18:59 Yep.

Christina Cacioppo 18:59 And of course, I, you know, I can say that, but like, is... They seem like they're more external than they probably are, and they're very experienced, so there's that bit. I also just think, and you- again, you know this better, but, like, in some ways, VCs just close more and get more practice, 'cause you're closing founders on deals, you're closing people for the company. You just have more reps on closing.

Jack Altman 19:17 It's just professional sales, basically.

Christina Cacioppo 19:18 Yes.

Jack Altman 19:19 Yeah.

Christina Cacioppo 19:19 And there's, like, a lot of pr- more practice.

Jack Altman 19:21 Yep.

Christina Cacioppo 19:21 A little bit of candidate support.

Jack Altman 19:22 That's a good point. I've actually never heard someone say it quite like that, but I think that's true.

Christina Cacioppo 19:25 You just, like, practice it more.

Jack Altman 19:25 'Cause I mean, founders are also closing all the time-

Christina Cacioppo 19:27 Yeah

Jack Altman 19:27 ... but it's like all VCs do.

Christina Cacioppo 19:29 Right.

Jack Altman 19:29 Yeah.

Christina Cacioppo 19:29 Yes.

Jack Altman 19:29 You're right.

Christina Cacioppo 19:30 Yeah.

Jack Altman 19:30 Yeah.

Christina Cacioppo 19:30 As much as I kind of, we talked about this, like-

Jack Altman 19:32 Yeah

Christina Cacioppo 19:32 ... hate it, and it offends the, like, rational person in me, like, VC brand matters.

Jack Altman 19:38 Yeah. Do you think that's the top thing?

Christina Cacioppo 19:39 Yeah.

Jack Altman 19:40 You think it just sprinkles a little fairy dust on everything and helps, like, self-fulfilling prophecy?

Christina Cacioppo 19:43 Yes, I think just, like, it's, like, all your conversion rates at every stage just get slightly better.

Jack Altman 19:47 And this is for, like, candidates, for customers, for the next funding round? Like, you think it-

Christina Cacioppo 19:50 For media. Yeah, it's like all-

Jack Altman 19:52 It just kinda hits everything?

Christina Cacioppo 19:52 ... everything just gets 10 to 30% better.

Jack Altman 19:54 Once you had Sequoia, did it make recruiting a lot easier?

Christina Cacioppo 19:57 Yes, in a way that we talked about. But, like, yes, in a way that I was, like, kind of, I don't know, annoyed by. But like-

Jack Altman 20:01 What's the dynamic?

Christina Cacioppo 20:03 We'd have... I don't feel like a literal person, but, you know, we'd have candidates, and we'd, like, approach them, and, uh, you know, Vanta's a little funny 'cause we raised our Series A at 10 million, but we'd be like: "Hey, we're this seed stage company, but, like, we actually have all this revenue, and, like, do you wanna come work with us? And we're YC." And someone would be like, "No." You know, and then, like- [chuckles]

Jack Altman 20:19 Yeah.

Christina Cacioppo 20:20 And then, and then, like, the next day- [chuckles]

Jack Altman 20:21 Like, that's not enough.

Christina Cacioppo 20:21 Yeah, no. [chuckles] Like, have fun over there.

Jack Altman 20:23 Next. Yeah.

Christina Cacioppo 20:23 Yeah, and then, like, the next day, we, like, announce the Series A from Sequoia, like 50 and 500, and then, like, the following day, we, like, follow it up and get-

Jack Altman 20:30 Everyone's in your inbox.

Christina Cacioppo 20:30 And can... Yeah, exactly.

Jack Altman 20:31 Yeah.

Christina Cacioppo 20:31 And you're like, "We are the same company."

Jack Altman 20:33 Right, except now you have a higher 409A.

Christina Cacioppo 20:35 Exactly. Like, now it is a worse economic deal for you.

Jack Altman 20:37 Yeah. Right.

Christina Cacioppo 20:38 But, like, if you wanna outsource your judgment to Sequoia, like, I guess I'm here for it. [chuckles]

Jack Altman 20:42 Yeah. Right.

Christina Cacioppo 20:42 Right?

Jack Altman 20:43 Did you experience it as, like, a one-time pop, or have you experienced it as, like, a durable lift?

Christina Cacioppo 20:47 Durable, and a, and in a way that I think I wouldn't have expected, but the, like, the brand and halo glow continues. And I should also say, like, I think Sequoia is very good at what they do-

Jack Altman 20:56 Yeah

Christina Cacioppo 20:56 ... and I'm very glad we worked together, and, like, all of that. Like, there's real stuff here, very real stuff here, and the brand halo just continues.

Jack Altman 21:03 Just dominates.

Christina Cacioppo 21:03 Yeah.

Jack Altman 21:04 Is there anything on the actual help besides closing candidates that you get a lot of value out of, or that you, even on a personal level, particularly value?

Christina Cacioppo 21:13 You know, kinda on the recruiting front, we get back channels and sometimes have, you know, their team... You know, sort of they are very good at knowing sort of everyone in the valley.

Jack Altman 21:21 Yeah.

Christina Cacioppo 21:22 Um, something they pride themselves on, but it's true. And so they are very... You know, there's, like, someone we're talking to, and, like, we don't have a lot of mutual connectivity and curious to talk to... You know, like, they-

Jack Altman 21:30 Someone on the team knows.

Christina Cacioppo 21:31 They're very good at-

Jack Altman 21:32 Yeah

Christina Cacioppo 21:32 ... at doing that. There was a period when you're, like, trying to raise the company's profile, and again, to the emails that don't get replied to, you know, you email, like, conference or reporter, and they're like, "You are one of 9,000," and, you know, "Next, please." We would, like, partner with Sequoia, and, like, Andrew and I would, like, do a conference together, and they'd like-

Jack Altman 21:50 Yeah.

Christina Cacioppo 21:50 We got on the conference stage 'cause of Andrew, you know, 'cause of Sequoia.

Jack Altman 21:52 Right.

Christina Cacioppo 21:53 Right? And I was just, like, the tagalong.

Jack Altman 21:54 Yep.

Christina Cacioppo 21:54 But there was some of that where that helped, too.

Jack Altman 21:57 That makes sense. I guess on the recruiting topic in general, maybe now unrelated to investors, but with your own recruiting, what have you found over time that that's changed for you or that has been important for you? But like, if you go back, you know, and you think about, like, how you recruited when you were a seed or Series A company-

Christina Cacioppo 22:15 [chuckles] So bad.

Jack Altman 22:16 I guess something changed, yeah, based on that.

Christina Cacioppo 22:18 I think in the early days, we were trying to be very frameworks-driven and rigorous, and everything was bespoke.

Jack Altman 22:24 Like your VC spreadsheet.

Christina Cacioppo 22:25 Exactly, yes.

Jack Altman 22:26 Yeah.

Christina Cacioppo 22:27 And it's like, you know, it's also when you've, like, you hire, like, the first person in every role, so every role is distinct.

Jack Altman 22:32 Yeah.

Christina Cacioppo 22:32 But we would have these, like, crazy, like, multi-day interview loops that were like we would send someone through a, I don't know, Tough Mudder, you know, and, like, wonder why candidates dropped out.

Jack Altman 22:42 Yeah.

Christina Cacioppo 22:42 And you're like, "Well, that's 'cause we asked them to, like, I don't know, do an obstacle course."

Jack Altman 22:46 Uh-huh, uh-huh.

Christina Cacioppo 22:47 I will say, the people who got through, like, man, were they down.

Jack Altman 22:49 They really wanted to join.

Christina Cacioppo 22:50 We're so down. [chuckles]

Jack Altman 22:50 Yeah.

Christina Cacioppo 22:50 They were really down. Um, but, like, in retrospect, you're like, "Wow, we made that really hard for candidates and us to, like, unclear ends."

Jack Altman 22:58 Yep.

Christina Cacioppo 22:59 Engineering recruiting, you just, you mess it up every two years, no matter what.

Jack Altman 23:02 Hmm.

Christina Cacioppo 23:03 It is hard. It is both hard and doable, and you just have to do it. So it's my... Talking to someone last night about this. And then you, like, figure out engineering recruiting for a bit, and then something changes.

Jack Altman 23:11 What changes? Inside the company or in the market, or what?

Christina Cacioppo 23:14 Both.

Jack Altman 23:15 Mm-hmm.

Christina Cacioppo 23:15 Well, like inside the co- Vanta example, we for years just hired generalists.

Jack Altman 23:20 Hmm.

Christina Cacioppo 23:21 And then, like, a year and a half ago or so, we're like, "Okay, cool, there we have a gen- we should have a generalist pipeline, but, like, man, we've, you know, we have Mongo. We should get people who really know Mongo. We use GraphQL, that technical section, whatever. We need people who know GraphQL," you know, and, like, we should have these, like, separate pipelines.

Jack Altman 23:34 In a way that this doesn't happen in design or sales or marketing? 'Cause, like, the tech stack changes in marketing, I guess.

Christina Cacioppo 23:39 You know what? I think what it is, is, like, engineering recruiting, I mean, to- is just harder than all the other roles.

Jack Altman 23:45 Yeah.

Christina Cacioppo 23:45 And the timelines are longer, and so when you break the pipelines, you just-

Jack Altman 23:49 Yeah

Christina Cacioppo 23:49 ... it takes longer to get them stood up again.

Jack Altman 23:51 Did you do work trials?

Christina Cacioppo 23:53 At that, yeah, in the early days.

Jack Altman 23:54 You don't now, right?

Christina Cacioppo 23:55 We don't.

Jack Altman 23:55 Yeah.

Christina Cacioppo 23:56 We don't now. We do, are gener- especially for, like, leadership roles of, of many sorts, we generally do just send them a bunch of data and information from what the role would be.

Jack Altman 24:07 Hmm.

Christina Cacioppo 24:08 And the project is usually like, "So, uh, we dumped a Google Drive of stuff on ya. Like, what should we do?" And, like, there's very binary responses to that. There's people who are like, [chuckles] like, "What do they want here?"

Jack Altman 24:18 Yeah.

Christina Cacioppo 24:18 "Like, this is madness." And people are like, "Oh, well, this is illuminating at least."

Jack Altman 24:22 Mm-hmm.

Christina Cacioppo 24:22 "You know, and I can, like, opt in or opt out."

Jack Altman 24:24 Yeah.

Christina Cacioppo 24:24 But we try to do very-... specific example, recruiting our CRO, so it's three years ago. Her thing was we sent her seven gong calls, top reps, middle-of-the-pack reps, bottom reps. We're like, "Here's your team! What do you think?"

Jack Altman 24:39 Oh, wow, and you're trying to see, like, can they tell from the gong calls accurately?

Christina Cacioppo 24:43 Kind of, and also, like, this is literally the team you're gonna get handed.

Jack Altman 24:45 Yeah.

Christina Cacioppo 24:46 Like, if you wanna- if you don't like this, like, let's just get that out now.

Jack Altman 24:49 Yeah.

Christina Cacioppo 24:49 Like, and so we don't have to, you know, be like, "Oh-

Jack Altman 24:51 Oh, that's smart

Christina Cacioppo 24:51 ... we have varying skill sets on the team." You know, you're like, "Here they are."

Jack Altman 24:53 Yep.

Christina Cacioppo 24:54 And, like, again, this is, this is the, the range.

Jack Altman 24:57 Yeah.

Christina Cacioppo 24:57 She stood out for many reasons, but part of it, she watched those, and she's like, "Oh, here's what I saw. Here's what we do," like the d- you know, like, unfazed and, like, very clear-eyed-

Jack Altman 25:05 Mm-hmm

Christina Cacioppo 25:05 ... and broke it down.

Jack Altman 25:06 Have you been, like, the type of CEO who wants to, like, be in every loop forever?

Christina Cacioppo 25:11 [chuckles]

Jack Altman 25:11 Or did you let that go at some point? To what degree do you distribute decision-making on recruiting?

Christina Cacioppo 25:16 Yeah, yeah. So actually, back to the early days, we saw that we had a principals interview.

Jack Altman 25:19 Yeah.

Christina Cacioppo 25:20 You know, Vanta interview, and I did those probably up until we were about fifty people, all of them. And then, like, I did have a team intervention where people were like, "Christina, you are spending too much time on this. Stop doing it."

Jack Altman 25:31 Yep.

Christina Cacioppo 25:32 And so I, like, distributed it. I should not have done that.

Jack Altman 25:34 Ah.

Christina Cacioppo 25:35 I think you should go through two, maybe three team interventions.

Jack Altman 25:38 Yeah.

Christina Cacioppo 25:39 Not the first one.

Jack Altman 25:39 Yeah.

Christina Cacioppo 25:40 You don't give it up after the first, at least the second.

Jack Altman 25:42 Yep.

Christina Cacioppo 25:42 So I should've hung on to that a little bit longer.

Jack Altman 25:44 Like, hang on till it's, like, two hundred people, you think? Like, when, when do you think it's at... Like, what's your now assessment of, like, when it's, like, enough is enough?

Christina Cacioppo 25:51 When you're spending probably more than a day and a half of your five days-

Jack Altman 25:54 Yeah

Christina Cacioppo 25:55 ... on it.

Jack Altman 25:55 And when did that come for you?

Christina Cacioppo 25:57 See, I didn't get there, 'cause I-

Jack Altman 25:58 Oh, so you were less than that

Christina Cacioppo 25:58 ... I capitulated after the first intervention.

Jack Altman 26:00 I see. Which was a-

Christina Cacioppo 26:01 Which is probably, like, three-quarters of a day.

Jack Altman 26:02 Got it. Okay.

Christina Cacioppo 26:02 Yeah, yeah, yeah.

Jack Altman 26:03 So maybe you could've gone twice as far.

Christina Cacioppo 26:04 Yeah, I think you should, like, at least wait for two interventions. [chuckles]

Jack Altman 26:06 Yep.

Christina Cacioppo 26:06 But then, what I started doing six or nine months ago is now I do do that for every director-plus candidate.

Jack Altman 26:11 Mm-hmm.

Christina Cacioppo 26:12 So I, like, reinserted myself.

Jack Altman 26:13 And they can't get in without your blessing?

Christina Cacioppo 26:15 Mm, I'll do non-blocking noes.

Jack Altman 26:17 Yeah.

Christina Cacioppo 26:17 And, like, they're, they're truly non-blocking, and it's like, "Here's what I saw-

Jack Altman 26:20 Yeah

Christina Cacioppo 26:20 ... if you as the manager-"

Jack Altman 26:21 You're like, "I wouldn't do this, but I'll support you."

Christina Cacioppo 26:23 Yeah, and, like, "Here are the gaps, and, like, if you as the manager, like, think you got this, cool. I will hold you to that. But if you wanna make this call, like, make it."

Jack Altman 26:30 When you do that, does it usually go through or not go through?

Christina Cacioppo 26:33 Yeah, it's a good... It's like, are they actually non-blocking? Um-

Jack Altman 26:35 Yeah, exactly, or are people like, "I probably shouldn't do it"?

Christina Cacioppo 26:37 Usually they're like, "I shouldn't do it."

Jack Altman 26:39 Yeah. Has it ever-

Christina Cacioppo 26:39 But more of them should go through. Yeah.

Jack Altman 26:41 Has it ever happened-

Christina Cacioppo 26:42 Yeah, that they go through

Jack Altman 26:42 ... that it's gone through?

Christina Cacioppo 26:43 Yeah.

Jack Altman 26:43 And that it's been good?

Christina Cacioppo 26:44 Yeah.

Jack Altman 26:44 Yeah.

Christina Cacioppo 26:44 Totally.

Jack Altman 26:45 Yeah.

Christina Cacioppo 26:45 Yeah, yeah, yeah.

Jack Altman 26:46 That's good.

Christina Cacioppo 26:46 Totally.

Jack Altman 26:46 Yeah, that's a good sign.

Christina Cacioppo 26:47 Yeah.

Jack Altman 26:47 Yeah.

Christina Cacioppo 26:47 No, more people should, like... Yeah.

Jack Altman 26:50 You do a lot of angel, or you do some angel investing, let's say, at least. When you're thinking about if you want to back a founder versus if you wanna hire somebody-

Christina Cacioppo 26:58 Yeah

Jack Altman 26:58 ... obviously, you're looking for both people to be talented and capable and, you know, whatever else, but, like, how different is the texture of what you're looking for?

Christina Cacioppo 27:06 Pretty different.

Jack Altman 27:07 Yeah.

Christina Cacioppo 27:08 Um, 'cause I think there's a lot of, like, how we work stuff at Vanta that have, like, kind of been baked into the culture, and, you know, there have been very talented people-- Actually, some of how we get the questions and the, the pieces of the principal interview is you, like, the very talented people who don't work out at the company and trying to keep that apart. Anyway, so there's, like, a whole thing there-

Jack Altman 27:25 Yeah

Christina Cacioppo 27:25 ... that I just, like, don't care about when you're angel investing.

Jack Altman 27:27 Right.

Christina Cacioppo 27:27 'Cause people don't have to work at Vanta. They don't have to work with me. Like, doesn't matter.

Jack Altman 27:30 Mm-hmm.

Christina Cacioppo 27:30 They can, you know, go do themselves in the universe.

Jack Altman 27:32 So basically, the culture, there's no culture interview-

Christina Cacioppo 27:34 No

Jack Altman 27:34 ... basically. It doesn't matter.

Christina Cacioppo 27:35 No.

Jack Altman 27:35 Does that make it easier then? Because at Vanta, you need to both be good, and you need this-

Christina Cacioppo 27:39 I think so, yeah.

Jack Altman 27:40 Yeah. So you'd invest in somebody before you hired them, basically?

Christina Cacioppo 27:43 Yeah.

Jack Altman 27:43 Yeah.

Christina Cacioppo 27:44 Totally.

Jack Altman 27:44 Yeah.

Christina Cacioppo 27:44 'Cause they, like, deeply, there's, like, lots of ways to build these companies, and, like, Vanta i- you know, I think there's a, it's, it's a, like, meta version of the, the gong call sales example is, like, people should just know what they're opting into.

Jack Altman 27:57 Yeah.

Christina Cacioppo 27:57 And we try to do that in our interview process and be like, "This can be for you, it can not be for you, but here's what it is," and it's kind of, not immovable, but, like, it's not gonna turn hundred eighty degrees.

Jack Altman 28:05 Yeah.

Christina Cacioppo 28:06 Whereas, like, somebody can build a company in a totally different way.

Jack Altman 28:08 Have you basically learned that a talented person who doesn't fit the culture, just it doesn't work out anyway?

Christina Cacioppo 28:13 Yes, yes.

Jack Altman 28:13 Like, you've tried it, and it just doesn't go the way you want it to-

Christina Cacioppo 28:15 Yeah

Jack Altman 28:16 ... for, uh, on either direction.

Christina Cacioppo 28:17 Yes.

Jack Altman 28:17 Yeah.

Christina Cacioppo 28:18 And so I think, you know, one of the things, info two years ago, we tried to get better at this, but was, like, just be hyper-transparent about what the thing that's in the interview process and hope, like, smart people will sort themselves out.

Jack Altman 28:28 Yep.

Christina Cacioppo 28:28 Some of it works, some of it doesn't-

Jack Altman 28:30 Yeah

Christina Cacioppo 28:30 ... but, like, that's- I do think we owe that to candidates.

Jack Altman 28:32 Yeah.

Jack Altman 28:33 I think one of the, one of the sort of interesting sort of secular things that's happened to Vanta and you is you started a company at sort of the tail end of cloud SaaS bull run, great, and then the world's all AI, everything, everywhere, all the time now. And so I'm curious how you've taken the moment and how you basically are running things, given that you have this obvious thing that comes in, and you obviously have to adapt. Like, what are, like, what are, like, the main things that have happened for you running the company now?

Christina Cacioppo 29:05 There is a lot of hopefully, like, AI encouragement and excitement across the company, and that is both in, like, how we work, like, our, you know, engineers using insert tool here. What are we building for customers? And I think, you know, really broadly, you know, like, we've got half of folks who are, like, totally down, and half of folks who are a little, like, "I have a job, and it's really busy, and, like, you want me to do what now? Like, can I just do my thing here?"

Jack Altman 29:28 Yeah.

Christina Cacioppo 29:28 And so it's like, okay, how do you, how do you bring those together? Um, and, like, what are the carrots? And so... But I think at the my level, leadership level, there is just, like, a ton of, uh, conviction that, like, this is real.

Jack Altman 29:41 Does it matter for your product, or does it matter for just what you're- the way you're building, the way you're doing go to mar- Like-

Christina Cacioppo 29:46 I think it matters a ton for our product-

Jack Altman 29:48 Yeah

Christina Cacioppo 29:48 ... because so much of compliance is taking information in one format and putting it in another.

Jack Altman 29:52 Yeah.

Christina Cacioppo 29:53 Right? Like, actually, and so there's just... And, like, I think the pieces of compliance will not change, but, like, will you have to... You probably, you or Eric, had to, like, write your own policy documents.

Jack Altman 30:02 Mm-hmm.

Christina Cacioppo 30:02 Isn't that, like, kind of, you know, you're like, "Yeah, and you also need to carry your patient."

Jack Altman 30:05 Yeah, or at least copy/paste them and hope they're right or something like that.

Christina Cacioppo 30:07 Exactly. Yeah, yeah.

Jack Altman 30:08 Yeah.

Christina Cacioppo 30:08 And then you're like, if you had to, if you want to know what was in them, you had to read them. [chuckles]

Jack Altman 30:10 Yeah, that's crazy.

Christina Cacioppo 30:11 Right? [chuckles]

Jack Altman 30:11 Yeah, now you can just skip the summary.

Christina Cacioppo 30:13 Exactly.

Jack Altman 30:13 Yeah.

Christina Cacioppo 30:13 You know, but, like, literally, like, we have all that stuff in the product now. That's a very small example, but I think it's a concrete one.

Jack Altman 30:18 Yep.

Christina Cacioppo 30:18 And so it's like, yeah, there's still be policy documents, but, like, how will they be created? How will they be disseminated? How do you know what's in them? How do you keep them in sync with everything else?

Jack Altman 30:26 Yeah.

Christina Cacioppo 30:26 Like, that is all AI.

Jack Altman 30:27 How much AI are you consuming, just, like, other AI products, just to run your company differently across everything?

Christina Cacioppo 30:32 [chuckles] We're, we're in an AI procurement boom. I hope I don't say this in a billion emails.

Jack Altman 30:37 Are you buying it? Yeah.

Christina Cacioppo 30:37 Yeah, but a little bit. We used to be much stingier, and I think- [chuckles]

Jack Altman 30:41 If you're selling an AI product, here's Christina.

Christina Cacioppo 30:42 I know. [chuckles] christinacaci@vanta.com.

Jack Altman 30:44 Yeah, exactly.

Christina Cacioppo 30:45 Please don't. [chuckles] ... but I think the thing we have actually, like, now it's a large enough company where you have to somewhat be thoughtful here. And what we're trying to do is like, okay, let teams do what they wanna do-

Jack Altman 30:57 Yeah

Christina Cacioppo 30:58 ... and procure the tools, and then have a forum for it, which is like IT kind of runs, and be like, "Okay, now we all come together," and be like, "Oh, we bought five meeting recorders?"

Jack Altman 31:05 Right.

Christina Cacioppo 31:06 "Cool, let's-

Jack Altman 31:06 Let's pick one.

Christina Cacioppo 31:07 "Let's figure it out," and but, like, do that incrementally along the way.

Jack Altman 31:09 So do you prefer people to... Would you prefer that s- AI gets to you bottoms up, that the best product wins through the team, rather than somebody trying to come sell you top-down with no usage?

Christina Cacioppo 31:19 Yes. Yes, now, because I think we, we were trying to do the top-down, no usage, and we're not making good tooling decisions.

Jack Altman 31:26 Interesting.

Christina Cacioppo 31:27 Yeah.

Jack Altman 31:27 Yeah.

Christina Cacioppo 31:28 And, like, again, I can, like, critique and be like, "Oh, we should think more of the GMs and our procurement," but, like-

Jack Altman 31:32 Yeah

Christina Cacioppo 31:33 ... that is not where the effort goes. [chuckles]

Jack Altman 31:34 Yeah.

Christina Cacioppo 31:34 Yeah.

Jack Altman 31:35 Yeah. Do you want to use basically as much as possible?

Christina Cacioppo 31:39 Yes.

Jack Altman 31:39 Like, yeah. Okay.

Christina Cacioppo 31:40 Yeah. There was actually a, a, this is kind of a cute phrase, but we were going back and forth about how many ChatGPT licenses we have, 'cause ChatGPT licenses were, like, kind of expensive, and Gemini is free.

Jack Altman 31:50 Yeah.

Christina Cacioppo 31:50 And, like, so can we just, like, be stingy about ChatGPT licenses and make everyone use Gemini, basically?

Jack Altman 31:54 Hmm.

Christina Cacioppo 31:55 And the answer is no. Um-

Jack Altman 31:56 It's not worth it.

Christina Cacioppo 31:57 Yeah. Well, so it's like unused ChatGPT licenses are very expensive. Used ones, they're actually pretty cheap.

Jack Altman 32:02 Right.

Christina Cacioppo 32:02 Right? And so it's like, okay, can you, like, get the energy focused on, like, getting the licenses used versus, like, being parsimonious

Christina Cacioppo 32:09 about them?

Jack Altman 32:09 What are some of the... I was about to ask this question in an obnoxious way of like, "If you had to start a startup right now, what would you start?"

Christina Cacioppo 32:14 Yeah.

Jack Altman 32:15 Which I'm gonna ask a different way. What pieces of software do you think that you could be or should be consuming that you're not yet? Like, what are some of the areas of the business at Vanta that you think should be AI-ified?

Christina Cacioppo 32:25 I think go-to-market systems is a Rube Goldberg machine constructed by, like, seven different tools.

Jack Altman 32:33 Yeah, that's what we had, and we had, like, nine biz ops people-

Christina Cacioppo 32:36 Yes

Jack Altman 32:36 ... holding it all together.

Christina Cacioppo 32:37 Exactly, yes.

Jack Altman 32:37 Yeah.

Christina Cacioppo 32:38 Yeah.

Jack Altman 32:38 And it was like, "Once it gets to that system, they're gonna grab this ball and put it over here." [chuckles]

Christina Cacioppo 32:42 Exactly. [chuckles] Exactly. And it's just kind of nuts 'cause you're like, "Okay, if this were engineering," like, or, "This does not exist in engineering"-

Jack Altman 32:48 It would be unacceptable.

Christina Cacioppo 32:49 It would be entirely unacceptable.

Jack Altman 32:50 Yeah.

Christina Cacioppo 32:50 It would be unacceptable a decade ago.

Jack Altman 32:51 Yeah.

Christina Cacioppo 32:52 And so, like, someone should fix that. [chuckles]

Jack Altman 32:53 Yeah, yeah.

Christina Cacioppo 32:54 完 全 に .

Jack Altman 32:54 Can you say a little bit more about the... Like, can you... D- you don't have to name the vendors, but like-

Christina Cacioppo 32:58 Yeah

Jack Altman 32:58 ... name the parts of, like, maybe the parts of the funnel you're talking about?

Christina Cacioppo 33:01 Yeah, like, I don't even mean the marketing b-

Jack Altman 33:02 Yeah.

Christina Cacioppo 33:02 It's like someone goes to vanta.com and is like, "Okay, I want a demo," or-

Jack Altman 33:06 Yeah

Christina Cacioppo 33:06 ... "I want Vanta."

Jack Altman 33:07 Yeah.

Christina Cacioppo 33:07 And then, like, how does that get to a sales rep, or how does that get to closed one? And like, oh, man, we got, we got... The ball, the balls are-

Jack Altman 33:14 It's all over

Christina Cacioppo 33:14 ... going into the tubes. [chuckles]

Jack Altman 33:15 Yeah. [chuckles]

Christina Cacioppo 33:15 Or onto the floor.

Jack Altman 33:17 Yeah, I never understood why it had to be so messy. Like, I get that it's kinda complicated and-

Christina Cacioppo 33:20 And then you have, like, race conditions between the tools-

Jack Altman 33:22 Yeah

Christina Cacioppo 33:22 ... and you're just like, "How does anyone-

Jack Altman 33:24 Yeah, that's good

Christina Cacioppo 33:24 ... put up with this?" Everyone puts up with it.

Jack Altman 33:26 Yeah.

Christina Cacioppo 33:26 Kinda nuts.

Jack Altman 33:27 Okay, that's good. What else?

Christina Cacioppo 33:28 Um, collections, contract terms.

Jack Altman 33:31 Mm.

Christina Cacioppo 33:31 It is, like, the least favorite part of everyone's job, including the, like, the, our customers, right?

Jack Altman 33:36 You'd think AI would be really good at that.

Christina Cacioppo 33:38 Yes.

Jack Altman 33:38 Like parsing the document, doing the perpetual reach-outs to people.

Christina Cacioppo 33:41 Yes, and, like, we've got some of it, but it's, it's, like, rules-based and doesn't work-

Jack Altman 33:45 Yeah

Christina Cacioppo 33:45 ... and people miss the emails, and, like, oh, and then it's, like, heightened emotions-

Jack Altman 33:49 Mm-hmm

Christina Cacioppo 33:50 ... and, like, oh, boy.

Jack Altman 33:51 Yeah.

Christina Cacioppo 33:52 Support kind of, or, like, the, like, I... Something is not working or-

Jack Altman 33:56 In support?

Christina Cacioppo 33:57 Yeah.

Jack Altman 33:57 The customers, just regular customer support.

Christina Cacioppo 33:59 Customer support.

Jack Altman 33:59 You're saying that the, the chatbots are not working well? Is that what you're saying?

Christina Cacioppo 34:03 Some of them.

Jack Altman 34:04 Yeah.

Christina Cacioppo 34:04 Yeah, uh, or I think we have some of that, and then I think we have, uh-

Jack Altman 34:09 Or is it the s- the tooling around them and, like, the reporting on it? Is that the issue?

Christina Cacioppo 34:13 I do want a lot of this stuff to go further. So one thing we have built is just a, like, custom GPT for, like, the Vanta tone of voice.

Jack Altman 34:20 Mm.

Christina Cacioppo 34:21 We call it Ilma Bot, 'cause Ilma is our Obama's name. But, you know, it's like our, our copywriters can only do so much.

Jack Altman 34:27 Yeah.

Christina Cacioppo 34:27 And so how do you kind of Vantify the writing?

Jack Altman 34:29 Yeah.

Christina Cacioppo 34:29 And I think that's works very well for marketing copy. I kind of want it for, like, all support tickets.

Jack Altman 34:33 Yeah.

Christina Cacioppo 34:33 And honestly, like, all customer comms.

Jack Altman 34:35 Yep.

Christina Cacioppo 34:35 Um, but-

Jack Altman 34:36 Do you think sales will get AI-ified?

Christina Cacioppo 34:39 Somewhat. I think there will be reps, but, like, even, like, we actually, I think, are quite good at enforcing Salesforce hygiene amongst our reps. You know, so, like, it works, but, like, ooh, how much time these folks spend-

Jack Altman 34:53 Yeah

Christina Cacioppo 34:53 ... you know, filling out command plans. And look, there's a part where you're like, you do actually want them to know the command plan-

Jack Altman 34:57 Yeah

Christina Cacioppo 34:57 ... 'cause that's what they're supposed to go execute on.

Jack Altman 34:59 Have you had any luck with, like, AI SDRs?

Christina Cacioppo 35:01 No, we haven't really tried. We tried a little bit, but we haven't... We're not a good-

Jack Altman 35:04 Yeah.

Christina Cacioppo 35:05 Still walking up the, like, hierarchy of SDR tooling.

Jack Altman 35:07 Yeah. What else? Anything in, like, security or operations or anything like that?

Christina Cacioppo 35:11 I think the, like, security operations center, the, like, other SOC, SOC-

Jack Altman 35:14 SOC

Christina Cacioppo 35:15 ... Yeah, another kind of SOC.

Jack Altman 35:16 That's confusing. That's frustrating.

Christina Cacioppo 35:17 Space.

Jack Altman 35:18 Yeah.

Christina Cacioppo 35:18 You know, like, the old way to solve that is put a bunch of people in the room, in a room, maybe in your company, maybe outsourced, that, like, look at alerts all day.

Jack Altman 35:24 Yeah.

Christina Cacioppo 35:25 Um, and then, like, the ten-years-ago Dropbox way was, like, write a bunch of rules and, like, kind of... But I think there's a bit of like, okay, that was, like, the rule-writing phase. How do we just AI-ify what is important, what is not? And that's hard, and you don't wanna mess it up, but, like, turns out, you know, again, hardworking people working all the time, staring at alerts-

Jack Altman 35:41 Yeah

Christina Cacioppo 35:41 ... all the time also mess it up.

Jack Altman 35:42 Yep.

Christina Cacioppo 35:43 And so how do you do that? [chuckles]

Jack Altman 35:45 What about, like, marketing, very top of funnel? Any, has anything, like, changed there?

Christina Cacioppo 35:49 Like, the LLM, SEO stuff, whatever you call it, AI EO or whatever people are calling-

Jack Altman 35:55 GEO?

Christina Cacioppo 35:55 Yeah, okay.

Jack Altman 35:55 Is that it?

Christina Cacioppo 35:56 Yeah.

Jack Altman 35:56 Some- I don't know.

Christina Cacioppo 35:56 Some-

Jack Altman 35:56 Maybe you're wrong.

Christina Cacioppo 35:57 But that thing-

Jack Altman 35:58 Yeah

Christina Cacioppo 35:58 ... is, I think, like, very real. We actually see impressions on our keywords dropping. Uh, it's like we might have, like, the same or higher impression share, the same or higher, like, CPMs or CBCs, but, like, overall, seems like search volume is dropping, and, like, we see that-

Jack Altman 36:14 That's crazy

Christina Cacioppo 36:15 ... in our SEM spend.

Jack Altman 36:16 That's really crazy.

Christina Cacioppo 36:17 Yeah.

Jack Altman 36:17 And your assumption is basically that's all just gone to the LLMs?

Christina Cacioppo 36:20 Yes.

Jack Altman 36:21 Yeah.

Christina Cacioppo 36:21 Yeah. Yes.

Jack Altman 36:22 That's just, like, a whole new work stream, I guess.

Christina Cacioppo 36:24 It seems like it, and you probably know the tools better than I do, but when I kind of poke around, it seems like a lot of the tools or work is, like, you just keep repeatedly run the same query in a bunch of tools, and then, you know, like, write down where, you know, like, how you do-

Jack Altman 36:37 Yeah

Christina Cacioppo 36:37 ... and then you rerun it the next day, and you rerun it, you know. I'm sure someone will build a bot thing, but, like, oh, boy.

Jack Altman 36:42 Is there anything else in, like-... HR, like, people stuff-

Christina Cacioppo 36:46 Mm-hmm.

Jack Altman 36:47 -or anything in finance or-

Christina Cacioppo 36:48 Oh, we did something, like, maybe moderately controversial. I'm curious for your take.

Jack Altman 36:52 Hmm.

Christina Cacioppo 36:52 Was we actually encouraged and wrote a, built a, like, or prompted a, a custom GPT, but for managers to use in perf reviews.

Jack Altman 37:00 Hmm.

Christina Cacioppo 37:00 Yeah.

Jack Altman 37:00 To, to help them give feedback?

Christina Cacioppo 37:02 Yeah.

Jack Altman 37:02 Yeah, I think that's good.

Christina Cacioppo 37:03 And yeah, 'cause it's kind of like, uh... Or I think my, I don't know my general thing, you have much smarter ideas, but, like, my general thing on perf reviews is, like, three sixties and perf reviews are super helpful if you actually do them.

Jack Altman 37:13 Yeah.

Christina Cacioppo 37:13 If you kinda do it halfway, it just ends up taking sixty hours from everyone's time-

Jack Altman 37:17 Totally

Christina Cacioppo 37:17 ... and being terrible.

Jack Altman 37:18 Totally.

Christina Cacioppo 37:18 And so, like, you know, you either need to go, like, all in or, like, all out. [chuckles]

Jack Altman 37:22 Yeah.

Christina Cacioppo 37:22 And so how do you get it? Yeah.

Jack Altman 37:23 My whole thing with, with performance reviews is basically it's like what you're trying to get to is a shared, agreed, you know, nugget of insight about what could be better, and maybe that takes three hours to get there, maybe takes thirty minutes to get there, maybe it never gets there, but I think oftentimes doing the work to get there is important. But really, what you need is just, like, a consolidated insight that both the manager and the person being reviewed are like, "Yeah, that is something I need to get better at."

Christina Cacioppo 37:47 Yep.

Jack Altman 37:48 So however you get there.

Christina Cacioppo 37:48 Right, however you get there.

Jack Altman 37:49 Yeah.

Christina Cacioppo 37:50 And, like, get there and get it clearly articulated-

Jack Altman 37:52 Yeah

Christina Cacioppo 37:52 ... and, like, that thing.

Jack Altman 37:53 It's not so dissimilar from, like, the way a lot of consumers are using AI for, like, kind of, like, borderline therapy or just-

Christina Cacioppo 37:59 Yep

Jack Altman 37:59 ... straight-up therapy type uses-

Christina Cacioppo 38:00 Right

Jack Altman 38:00 ... where it's like, you know, maybe a human's better in some ways, but just getting to the, like, "Here's an insight that's useful"-

Christina Cacioppo 38:06 Yep

Jack Altman 38:06 ... is worth a lot.

Christina Cacioppo 38:07 Right. Right, and, like-

Jack Altman 38:08 Hopefully it's a good one, but yeah

Christina Cacioppo 38:08 ... I can read it and, like, think about it, and agree or disagree, but, like-

Jack Altman 38:12 It's obviously conditioning

Christina Cacioppo 38:12 ... I got it.

Jack Altman 38:13 Yeah.

Christina Cacioppo 38:13 Yeah.

Jack Altman 38:13 Just has to be a useful insight, but if it gets there, which it seems like in a lot of cases it does-

Christina Cacioppo 38:17 Right

Jack Altman 38:17 ... it's, it's really good.

Jack Altman 38:18 The last topic I wanna go to is, so you're what, seven years in, eight years-

Christina Cacioppo 38:22 Something like that

Jack Altman 38:22 ... something like that?

Christina Cacioppo 38:23 Yep.

Jack Altman 38:23 What's the founder sort of mindset that you've, you know, settled into? Not that you're settled into one, and I'm sure there's still-

Christina Cacioppo 38:30 Yeah

Jack Altman 38:30 ... turmoil and evolution, but, like, what is the inner game journey that you've been through?

Christina Cacioppo 38:34 Yeah. Uh, two things. The, like, trope of, like, a dozen could do three, you just go faster, is deeply true, and I think the lived experience is, like, you know, kinda every day you... I don't know, like, I feel like I, like, only halfway know what I'm doing-

Jack Altman 38:46 Yeah

Christina Cacioppo 38:46 ... or, like, that's a new skill. And so you're- you never feel like you're, like, on it. I feel like I'm totally on it, but then every once in a while, I'll, like, go back and, you know, someone's out, so I'll, like, do the one-on-ones with their manager and be like, "Oh, I can do this now," right? And the first time I was managing or managing a manager, I didn't feel-

Jack Altman 39:02 Yeah

Christina Cacioppo 39:02 ... comfortable, but, like, I got- I did learn something.

Jack Altman 39:06 Yeah.

Christina Cacioppo 39:06 And you have these kind of moments, which is one of, like, talking to an early-stage founder, and you're like, "Oh, no, I, I have a point of view here, and I adamantly believe it. Maybe I'm right, maybe wrong, but, like, I've learned something."

Jack Altman 39:17 Yep.

Christina Cacioppo 39:17 So there's some of that. Uh, even if in the day-to-day, you're, like, still and like, "Well, I've done this before, but here we go."

Jack Altman 39:22 Yep.

Christina Cacioppo 39:23 And then I think there is a... all the, like, there's, like, different types of CEOs or, like, the job changes, and your job is to, like, make the-- build the product and then build the company and then build the team-

Jack Altman 39:32 Yeah

Christina Cacioppo 39:32 ... or team, company, whatever it is.

Jack Altman 39:33 Yeah. [chuckles]

Christina Cacioppo 39:34 You know?

Jack Altman 39:34 Some order.

Christina Cacioppo 39:35 Some order. Not that-

Jack Altman 39:35 You did it

Christina Cacioppo 39:36 ... not that order. [chuckles]

Jack Altman 39:36 You just don't remember it. Yeah. [chuckles]

Christina Cacioppo 39:38 Probably product, team, company. Now that I said it out loud.

Jack Altman 39:41 Yeah.

Christina Cacioppo 39:41 And, like, those are very different, and there's, like, all different types of people. You enjoy different things, and, like, I think in some way that's true, but I also think, I don't, like, you know, joke that's kinda not a joke, is like, "No, you just have to, like, Stockholm syndrome yourself-

Jack Altman 39:53 Yeah

Christina Cacioppo 39:53 ... into being like, 'Well, I used to be someone who liked to build products.'"

Jack Altman 39:55 Yeah, yeah.

Christina Cacioppo 39:56 "But now I love building teams."

Jack Altman 39:58 Right.

Christina Cacioppo 39:58 "And whether or not I identify as that person as two years ago-"

Jack Altman 40:00 Like, now that's me.

Christina Cacioppo 40:01 "... doesn't matter. Now that's me, and I believe it," you know? And then, like, when it changes, you're like, "Now I'm this person."

Jack Altman 40:05 Yeah, yeah.

Christina Cacioppo 40:06 "I love HR policy," [chuckles] you know?

Jack Altman 40:09 Yeah.

Christina Cacioppo 40:09 " 'Cause that's what the company needs right now."

Jack Altman 40:10 Yeah, totally.

Christina Cacioppo 40:11 And, like, you know, joking but not, like, figuring out how to be like, "This is the game and the puzzle and, like, the journey, and I need to take joy in it, 'cause otherwise I will just, you know, like, be sad and burned out and unfulfilled and, like, this is not sustainable."

Jack Altman 40:24 Did you have a part of the journey where you, um, were both doing things that you didn't enjoy and hadn't yet figured out how to, like, control your own, like, mindset and emotions like that?

Christina Cacioppo 40:36 Yes.

Jack Altman 40:37 'Cause I imagine at the beginning-

Christina Cacioppo 40:38 Yes

Jack Altman 40:38 ... I mean, who doesn't love... I mean, everybody loves building a product. Everybody loves getting that early customer rush.

Christina Cacioppo 40:42 Right.

Jack Altman 40:43 Like, that stuff is just, like, objectively fun.

Christina Cacioppo 40:45 Yes.

Jack Altman 40:45 And then there are things that are, like, debatably fun, and some people might love them, but not everybody loves them.

Christina Cacioppo 40:49 Yes.

Jack Altman 40:50 Yeah.

Christina Cacioppo 40:50 And I think it's, and remember, this especially in the early days, 'cause, like, for me, the, the first version of this was, "Okay, we have this product and company and, like, recruited a couple engineers. Now I have to go, like, do all of go-to-market and both do it and recruit people."

Jack Altman 41:02 Yeah.

Christina Cacioppo 41:02 "And I didn't know how to spell go-to-market, like, kind of, actually.

Jack Altman 41:05 Yeah.

Christina Cacioppo 41:05 And so it was like, "I gotta do this. Everyone else is counting on me, um, to do it," and, like, "Wow, am I bad at it-

Jack Altman 41:10 Yeah

Christina Cacioppo 41:10 ... 'cause I've never done it."

Jack Altman 41:11 Yeah.

Christina Cacioppo 41:12 And, like, kind of raking myself over the coals for that.

Jack Altman 41:15 Mm-hmm.

Christina Cacioppo 41:16 And then sort of being like, "Okay, right, I'm bad at it 'cause I haven't done it. My job is to get good fast."

Jack Altman 41:21 Yeah.

Christina Cacioppo 41:21 Right? Like, it's, it's trajectory, not, you know, anything else, but, like, kind of reframing that.

Jack Altman 41:25 Did you do anything to get that sort of, like, self-control that you're now at, of being able to say, like, "I like this because I told myself I'm gonna like that?" Like, was there, like, you know, somebody you picked this up from? Was there-- did you, like, read a bunch of, like, Buddhist books?

Christina Cacioppo 41:39 [chuckles]

Jack Altman 41:39 Did you like something... You know, like, what did you do-

Christina Cacioppo 41:41 Yeah

Jack Altman 41:42 ... to get to that? 'Cause I think very few people have that kind of ability to tell themselves that, "This is how I'm gonna feel about this thing."

Christina Cacioppo 41:48 Yeah. I think a bit of, for me, it used to be runs.

Jack Altman 41:51 Mm-hmm.

Christina Cacioppo 41:51 I went long runs, like, four miles, you know, but it was just like... And I live by Golden Gate Park, and you're like... Also, when I'd get really frustrated or pissed off, I'd, like, go run-

Jack Altman 41:58 Yeah

Christina Cacioppo 41:58 ... usually at some point, so there was, like, some something. We have a mutual friend, J.Zack Stian, who is, like, very, who I think is a very helpful, like, playback, "Sounds like what you're saying-

Jack Altman 42:08 Yeah

Christina Cacioppo 42:08 ... sounds like this is a thing," you know?

Jack Altman 42:09 Yeah.

Christina Cacioppo 42:10 Like, or, like, prompting on self-reflection.

Jack Altman 42:12 Mm-hmm.

Christina Cacioppo 42:12 And then I think also just talking to other founders, right? And then you talk to the folks who are like, "Oh, I'm supposed to be building the company, but, like, I still just wanna build the product," and, like, "I'm really anno- you know, and I'm annoyed, and I'm unhappy," and just kind of being like, "Oh, that seems mad-"

Jack Altman 42:27 Yeah.

Christina Cacioppo 42:27 "... you know?"

Jack Altman 42:28 Yeah.

Christina Cacioppo 42:28 "But, like, I get it," right?

Jack Altman 42:30 Yeah. Absolutely. Well, um, Christina, this was really fun. Thank you for taking the time to do this. It was a, it was a blast for me.

Christina Cacioppo 42:35 Thank you so much for having me. [upbeat music]