The art of quitting

0:03This week on Great Chat, we're talking about the art of quitting. How do you know when to quit? Is there a right time to do it? Did someone hand you a playbook the last time you quit and does that same playbook work today? I'm Sally and this week we're joined by Helen and Ashley. This podcast is brought to you by Mercury, the fintech used by over 200 ,000 companies to simplify their finances. We're huge Mercury fans at Great Chat and we use it to run this podcast. A few of us are also current customers for our funds and startups, not to mention the dozens of founders we've backed as VCs, angels, and scouts that run their businesses on Mercury.

0:38If you're launching a startup or fund, visit mercury.com to apply online in 10 minutes or less. The onboarding couldn't be more intuitive or delightful. All right, hi guys. Hello from my new podcasting studio. I know, no one can beat this background. Yeah, for anyone who is listening, I am on a boat right now and it's in a harbor and I'm visiting my parents. And by the time you hear this podcast, I'll be back in New York. But their Wi-Fi at their house is terrible. They live on an island. But tethering from this harbor works. And so maybe this is like my podcasting hack when I visit my parents.

1:22You'll always see me on a boat. You'll know I'm with family. Are you on a Starlink? No, right? No, not a Starlink. Just like T-Mobile tethering. I think there's like a tower or something near here. I love it. I feel like we were promised Starlink on all the United's and we have issues getting connected on those airplanes. The best Wi-Fi apparently is on Burning Man on the fly. Oh, my gosh. Well, were we just talking about how Burning Man, depending on your like feed algorithm, was either like very dark and like homicide news heavy or it was like, I mean, I saw a lot of like best burn ever. And then I saw the baby that was born.

2:04Um, but yeah. And then, yeah, on Twitter, it sounds like Burning Man is like, you know, millennial cringe sort of activity, which means we should definitely go. But, um, Did you guys double click on the baby thing? Because it was a surprise baby. Like, neither parent knew that there was a pregnancy. And then like a baby was born. And like, they were both like, Oh, this is amazing. What a miracle. And I'm just like, I just don't understand how anyone I feel like we do read about that yeah I mean you you you this isn't like the first time um we've read a headline like that but as somebody who's given birth twice like I don't know the wild thing is I didn't it did not even hit my feet that there was a birth at Burning Man all I got was the the murder on the playa it's the polarization of of news it was crazy because the mainstream media coverage like all opens with like um a man was discovered in a pool of blood as people gathered around a wooden effigy and like let it lit it and i'm like oh my gosh this sounds like devil worship like if you don't know the rituals of burning man like it must sound so insane to be encountering um this festival through the lens of a murder well speaking of feeds um we were also talking about how I'm getting served nonstop sorority recruitment videos.

3:27And so, um, which one are you going to join? I am already part of Gamma Phi Beta. So love PKE everyone, but I was making this comment and yeah. So like, I can't get enough and, and like shout out to the, to the women at MIT who just also posted a fire video, like, you know, ever, you know, I don't see why they can't take part. but that reminded me of something that I said like a long time ago when it was like the Hunger Games era of like tech recruiting like I would say like late 2010s you know there's like so many hot startups are all fighting for talent and you started to see this role called like candidate experience manager pop up at places and I made this joke that everything I ever learned about tech recruiting I learned at sorority rush.

4:18And that sounds funny, but it's like one of the like cardinal rules that I remember was every girl, whether or not, you know, you think that they are a fit needs to believe that they are going to be getting a bid on bid day from your sorority. And the reason for that is because freshman girls, when they rush, like they all go back to their dorms and they all talk about, you know, who they're ranking and, and which houses they liked. And if they feel like they're not going to get a bid from you, then they're going to like hedge and like talk shit, right? Because they don't want to like say that they're going to, that they love the sorority and then they don't get a bid and it's like crushing.

4:56So they want to just like, you know, like hedge and be like, oh, I didn't want them anyways. And that is not what you want. And I feel like similarly at startups, right? Like candidate experience is so important, And even, you know, even if it becomes like clear during the middle of the of the like, you know, batch interview, you know, that that this person is probably not going to work out. Like it's really important to give everybody a really great experience. And I feel like a conversation I've had with founders is often like, no, we have to let people know that like they're not a fit, that they're not going to cut it.

5:29And I'm like, what good does that do for anybody? But anyways, that was like the thing that I remembered. and I am going to continue to watch all these Rush videos for like probably another couple weeks. I went to NYU so I missed out on the whole sorority thing. I don't think we had any sororities. I think we had one like business frat and I had just moved from Australia. I mean everything is subjected from a lens to whoever I want to see it. So the only acclamation I had to U.S. culture and sororities was I think 10 Things I Hate About You. Oh, were there sororities in that? I thought that was like a high school movie.

6:04Oh, no, you're right, you're right. Sally's still acclimating. Excuse her, it's a decades-long process. I went to Georgetown, and the only sorority option was the Foreign Service sorority, which I didn't judge, and it was kind of unfair. Like, the guys actually had a house, but there was no house for the ladies, so we just went to, like, guest speaker stuff, and then we were invited to parties at the embassies, which actually was pretty cool, but very nerdy, very Georgetown. Very D.C. But my best friend from high school went to UPenn, and I'd go visit her every year. And there was a real sorority culture there, and she was in a sorority.

6:45So I was like, it was crazy. I was like, how are our colleges? But did she live in the house? Because I've had friends that went to Penn State, and they said that there aren't sorority houses because in the state of Pennsylvania, there are still those laws about a certain number of women can't live together or else it becomes like a brothel or something. She actually did not live in the house, but the house was where all the parties were. That's right, exactly. And still a big part of her identity. Her friend group was like so tied to this sorority and I was like, oh, that's so crazy. And so different worlds.

7:20But I like the tech recruitment. Helen, I think you need to write that blog post. My favorite story of the week was that Anguilla is making millions off of.ai. so I don't know if you remember actually I didn't even know I was reading through it and I guess in the 80s everybody was issuing out dot you know whatever the country like two-letter symbol so like if it was Australia it's dot au and Korea dot kr and Anguilla is dot ai and every year they're making like millions of dollars I think they they paid they got paid 700 ,000 dollars for u.ai so i thought that was just fascinating a little nugget i think it's like tens of millions so it's it's real money for like a smaller country i like went down a little bit of a rabbit hole because i'm there have been other other things like this do you guys remember the trend when like every startup was dot ly so oh yeah it's like yes or whatever like grammarly which is why like yeah i don't know why grammarly did not take code as name when they acquired them well especially now that they have like a bigger tent and they're like acquiring all this stuff it's like grammar really feels like a very narrow value prop libya is dot ly so they benefited from that craze um dot me is montenegro and then the one near and dear to my heart dot vc is saint vincent and the grenadines so that's so great who knows who knows which countries will benefit next what were some other ones like dot co dot cc dot xyz yeah yeah i just don't i don't think it was like a big crypto one it was yeah all the dot xyz became dot ais like in a period of six months after like after chat gpt was launched so the other one that uh we've been chatting about was the post or one of many posts and then the sort of conversation around like 996 culture and how now you're locked in.

9:26It's 996. And what was it? Like lift, eat meat, marry young. I'm going to read it. It's excerpted from an article from SF Standard. The article is titled, Burning Man is for the Olds. Just ask the AI kids. Ouch. which, telling to your point, Burning Man is now Millennial Cringe. I've never been to Burning Man. No, I know. Sally's the only expert on this. Look at me, the resident burner. But a 23-year-old co-founder of an AI startup said, the current vibe is no drinking, no drugs, 996, which means working from 9 a.m. to 9 p.m., six days a week, lift heavy, run far, marry early, track sleep, eat steak and eggs.

10:13Um, so that is, that is like the Gen Z, uh, mantra. Yeah. So I feel like there's two conversations. One is like, okay, that that's insane. Also, Mary Young for what exactly? Um, uh, given that, that schedule. Um, and then the other is just this sort of broader question of whether, you know, uh, people posting this and talking about this, it's more, it's more performative than ever. and that there's always been a grand culture. But the thing that is different now is that people are posting about it. And I think we've talked about like different flavors of like hustle porn that we've seen. But I think now that there's a name like 996 or, you know, people really putting in job descriptions like that this is a 996 culture.

11:00Like, I think that's something that's kind of different. I also have two strains of thought on this one. And I feel like, I mean, I grew up parts of my childhood in Asia. And Asian culture is very, very much a 996 culture. It starts from middle school, high school. We would go to school. And then at the end of school, we would do these after-school curriculum that runs until midnight. And this is all the way until you get to college. And then it gets much worse. And you see a lot of burnout through that. And I think that's kind of what we're seeing in some of the cultures in Silicon Valley as well.

11:33And it's something like a lifestyle that like it at the time seems like you pack everything in, you jam everything in and you get so much done. But then you actually don't have when you don't have time to like process and think and pontificate on various things. I think there's there's a lot more downside to it. The other train of thought is I was just thinking about it as we're talking about is I don't know. In our 20s, I do remember the time where we are so excited about like working on something new, like super excited. and working hard, working late. And maybe there's some part of it that we should also embrace this hustle culture, but for the people that are really excited about it, it doesn't mean that everyone needs to be part of this culture, but also celebrate the ones who are really excited about it.

12:20Because I think when we were at that time, when we merged the passion of work and passion of time, I don't know, it was just a fun time. So that was my two trades of thought on that. Yeah, I think I said this a couple weeks ago, but I was talking to somebody who just left Meta, and they're an executive. And I was sort of like, he was talking about how insane the hours were and how he was in office six days a week. And I was sort of like, oh, well, you know, that's how it was when we worked together back in the day. And he stopped me, and he's like, yes, because we wanted to. And it was like this chilling sort of like, oh, okay, that was like a, we were so young, we had nothing else to do.

13:06We might as well live at the office and work all day, right? Because you're doing with friends and there's food and it's awesome. And he was more saying now it's like a very tops down, you know, sort of mandate for 4996. And I was like, oh, that is different. You're right. I actually think a lot of startups and founders that are like leaning into this and embracing it, they see it as an aspirational cultural thing that they're sharing. Like, come join this company and grind. And like, this is the dream versus this is the mandate. I think it feels like a mandate to people who aren't predisposed that way.

13:40But 100%, like 996, I'm sure I clocked that for most of my 20s. And it's great if people are excited. But Helen, I also agree that there's a large like performative aspect there and it's a little bit like my snarky thing is if I see people promoting their their relationship too much I'm like uh-oh and I feel the same way I feel the same way about people who are promoting how hard they're working so much and then also I don't know I just like we're in such a unique moment in technology right now and like yes there's a lot like you need to be heads down and execute, but you also need to like pull back.

14:19And like, like there's, there's so much space for imagination and the path forward is so nonlinear. And I feel like if the whole culture is around just like working 24 seven, like, are we going to get the ideas we need to get that come in those sort of like in between spaces? So that's my, if you want some cover to not work all the time, just say you're like, you know, you're dreaming up the future. And that can only happen on a run or in the shower. Okay. So for our big topic this week, we were talking about, and it's something that we talk about quite often because in our group chat, we'll just share links to like, you know, departure announcements or an article covering like a transition.

14:59And so I think one that caught our attention this week was Suhail Doshi, who's the founder of Mixpanel. In like, I think COVID era he founded a company called playground um he quit online and i'm sure he quit before that but i think he was just sort of like communicating that and and the note said there are better things to pursue with our collective time than designing casual graphics we ought to strive to work on more important things for humanity if we have the means and energy i'm unapologetic in how I will use my time here on earth. And I was like, that is quite, quite a, a, a quit note. And I think some useful context too, because in some ways it was even more dramatic how he quit.

15:47So this, the thing you just read was in response to someone asking him a question. So he tweeted out, I am now a free agent. He didn't even acknowledge what was happening with Playground, his company and someone was like, oh, like, can you give us a memo on like, like why you're leaving playground or why playground didn't work? And this was his like full throated response. And so I think it's like twofold. There's the piece of like, what responsibility do you have to thoughtfully communicate? Like shutting down a company or moving on from a company if you're a founder. And yes, Helen, let's assume he like communicated like previously to his investors, employees, all of that.

16:28And then the second piece is this very dramatic statement to unpack in terms of how one even makes these decisions and what his lens was for leaving playground to pursue other things. But yeah, definitely a fun way into this conversation. Yeah, because I mean, I think this is a founder example, but I think we are seeing more and more, I think, transitions in and out of venture. And then of course, operators, I feel like there's just a pretty steady cadence of that. And one thing that I think about because of the roles that I've held throughout my career, like exec comm departures definitely fell under my wheelhouse.

17:10And always, it was like, keep it as straightforward and positive as possible. And that was like, from first principles, every piece, every player, there's just nobody who benefits from anything anything otherwise, because you want people to stay focused and you want people to not think about their own departures when the time comes. Right. Because if there's a messy departure and, you know, now there's like a whisper train of something, people will start thinking like, oh gosh, well, when I leave, what if that happens to me? Right. And it's like, nope, you want everything to be happening, you know, with respect and dignity and just sort of like excitement for the future for everyone else, which is why it's such a nice reminder for me that But so few investors have operating experience because I think that that's generally understood within companies.

17:58But I feel like these days, and I don't know if it's because like we're around so many spin outs, but like I feel like if you're talking to somebody at a firm and, you know, remarking about how somebody has recently left and now they're starting a fund and that's so exciting. It's like they'll be the first to tell you, oh, they were pushed out. It's like, oh my gosh. Or, you know, I feel like I'm constantly in this position of being like sort of taken aback of like kind of hearing about the nitty gritty of like, you know, how people are leaving firms. And that is such a stark contrast to me in sort of like the other world that I know.

18:33But curious what you guys think about that. Yeah, I mean, Helen, I've obviously done like a ton of exact departures, including my own, over the years from a comms capacity. And I think the thing that people miss when they make statements like that is actually that that shows underlying insecurity rather than strength, right? Like if your firm is in a position of strength, if your company is in a position of strength, you can afford to be really gracious when someone leaves, whatever the circumstances are. And I think when people are on the defensive and feeling protective, that actually showcases, oh, you're like worried about this exodus.

19:10You're worried about the perception of the firm because this person left versus feeling really good about the bench that you have. And so I think it's a good reminder for companies like it's not just about being kind and gracious. It's actually like the way you are perceived will come through in these in these communications as well. Yeah. And actually, that's really interesting you said it that way. I remember we were just sharing some of the more notable departures in the last few months. And one that stood out to me after you mentioning is when Nat Friedman and Daniel Gross left their funds, Ilya Schvitzger put out a tweet right away being like, hey, I'm taking over control as CEO.

19:53and it felt very reactive then then like they actually had a plan in place and of course like a lot of these things like happen very quickly especially in this era where people are acquiring executives with huge sums of dollars in like two three-day periods but it felt very very reactive and then I'm curious also just like how they you know communicated that to their funds which I'm sure you guys have more visibility than I do um with there is I think it's called NFDG I forget what it stands for um that had a really initials oh obviously um but I'm curious like how when when when you have when you're two GPs at a fund and you're leaving like what do you and when do you communicate that to the LPs I think something similar might have happened with Jack Altman in his fund.

20:42So how do you... Well, Jack Olin is still running his fund. But I think you were talking about two things where it's like NFDG, yes, they raised a successful fund and they had this awesome accelerator too called AI Grant. And it sounded like they departed those. And I'm sure the LPs were first to be notified. So I'm kind of answering this question of like, what is the right course of action. I think LPs who are investors, you know, in that fund should be notified first. But also Daniel Gross was a co-founder of SSI, right? So like it was like dual comms. He's both leaving a fund and leaving a company.

21:25And I hope he's having a great time at Meta. But like, you know, I think that fund communication is a little different because none of it has to be public. You don't owe the public really anything. I'm sure there's for really high profile departures of like tier one firms, maybe there is some sort of exit statement. But I think that you have to assume most of the communication is just happening in a way that we can't see it. Yeah. And maybe to get even a little bit more granular, I'm sure they both had key person provisions, meaning if either of them were not fulfilling their commitments to the fund, they would have to notify LPs and that puts you in like a limited operations mode where you have to work with your LPs on a plan forward.

22:07And so that would actually give you some time too to figure out, okay, we think we're going to take this, like we're going to take this new role. Meta is offering this and you can sort of like work that out with your LPs. But yeah, if you're a fund manager, I mean, the expectation is you're there for the duration of the active investing period, which they had not, I think they deployed about like half their capital. And so their first obligation is to their LPs. And then of course, you also need to communicate to founders as someone who's gone through, I was at social capital when Mamoun Hamid and Ted Maidenberg left.

22:42There's a lot of communications to LPs, to founders, of course, to the team. And then like, to Helen's point, the public, the public comms sometimes is a forcing function for how quickly that all happens. But on the LP front, you need to do that right away. And I know some firms who've gotten in trouble for not doing that because it's such a huge, huge part of the trust. I mean, we've also seen some pretty high profile founder departures and even returns. So like fun stories. Yeah. Like Ryan Peterson obviously left Flexport and then came back pretty quickly. And then more recently, Ty Haney is returning to Outdoor Voices.

23:22And I guess she was kind of ousted from her company. So a little bit of different situation on the way out. But yeah, I think like a founder and CEO leaving is such a profound thing in the startup world, which is why these like acquisitions have been so strange where like, you know, the CEO is joining a new company, but the company shell still exists. And so we're like, you know, we're sort of in a new era of CEO departures and how those are communicated or not communicated. I think a lot of them have been done pretty poorly. Because what do you even say? Sorry, I got a really amazing offer. And so I'm just leaving you guys with this licensing deal.

24:02Well, I mean, that reminds me that in today's day and age, I feel like whenever you approach somebody who is sort of in a transition or thinking about transitioning, you know, thinking about leaving, they think in terms of the LinkedIn post. Does anybody else do that? Like when you're like thinking about a new job or thinking about like leaving, you're just like, oh, well, what would that, what will that announcement look like? And, um, it's hard today not to think in those terms as silly as that sounds. Right. And, um, you know, I've definitely had people approach me, and ask questions about like timing their departures and sort of the story around it where it's very obvious that that's like top of mind for them.

24:41And I think that, you know, something that we were trying to think back to all the time said that like we have departed companies in our careers. The things that all of our stories had in common was at the time, it just feels so outsized. Oh, what are people going to think? People are going to think this. People are going to think that. It's like, no one cares. Yeah. No one cares. And you can see that looking back, very hard to understand that at the time. And that's something that I wish I could have told my younger self. It's like, no one's paying attention to you. People are just stoked for whatever you're doing next.

25:15And, you know, like that's what you should be focused on the future. Yeah, I remember when I was at CNBC and NBC News and probably at the top of my career in the media world. And I was young and moving up the ranks quickly. And I think internally I was feeling very kind of complacent or there wasn't much like growth within the industry. And I knew that there was a lot of exciting things going on. So I made a bet to leave, but it took me probably two to three years to actually like have the guts to leave. And even in that communication process, when I decided to jump from a big media company to a smaller operator role at a company, not a ton of people knew.

25:59I was like oh my gosh what what are people gonna think how am I gonna try to like create this like narrative arc around like I went from doing all this are they gonna think that I like missed an opportunity and or I got pushed out and to your point Helen like nobody gives a shit you know and every and and and then you kind of redeem I wouldn't say redeem what's the word I'm looking for like a few years later they're like oh I see why you did that move and only you know the decisions you're making, whatever that like time of like how you felt working at this company or like where you want to be like five, 10 years from now.

26:36And so, yeah, I 100 % agree with you on that. I guess the one area I would push is I do think the comms are more delicate if you don't have your next thing lined up. Like, like comms around like, I think that's happening more, more lately, right? People don't have a plan. Right, right. More straightforward. And I mean, I've been in this place. So my first departure comms was much more straightforward because I was leaving Box where I'd been for six years, got the company through some really big milestones, had my successor on my team. It was very elegant. Actually, it was Aaron Levy who even told me to write a post about where I was going.

27:14So it was more about the opportunity versus leaving something because my identity was so intertwined with like the box brand. And so that was like, that was a very simple, clean comms. And then my next two departures were, you know, I left Social Capital before I had my next thing lined up. I left Glossier before I had my next thing lined up. I do think those are like a little bit more delicate. And, but at the end of the day, it's still the lesson is like, don't overcomplicate it. People aren't worried about this. And if you're like too defensive or worried, People will think you were pushed out.

27:49You don't want that energy coming through. And I remember social capital was especially hard because I left amidst a lot of change that was happening on the team and at the strategy level. A lot of eyes on it. Yeah, I knew it was the right thing for me to leave. I wasn't signing up for that next chapter, but I felt such a deep obligation to stay. because like when you're, I was the marketing partner in led comms and that's when you're needed the most, right? Like in a crisis or in a moment where there's a lot of public scrutiny and I had to talk to a mentor who was like, it's okay to make this decision for yourself.

28:27Um, and, and also even told me it was like very like female coded that I was so like ready to just like, you know, uh, hang on for the sake of the, for the sake of the business and my team. But the other piece that was helpful and that I learned there is if you are leaving during like a very public time, you actually don't need to do a lot of messaging. Like it will be clear. Like there were a lot of people, you know, that Chamath was very public about making changes. There were a lot of rumors. And so I got to keep my departure like very light, very fun, very gracious, like and not over message it.