What comes after the Girl Boss?

0:04Today on Great Chat, we celebrate International Women's Day by sharing how anyone can help women in their careers. And surprise, it has nothing to do with a thousand word social media post or turning your profile picture or office pink. I'm Helen, and this week I'm joined by Ashley. Great chat is brought to you by Mercury, radically different banking loved by over 300 ,000 entrepreneurs. We use Mercury to run this podcast and love recommending it to other founders and fund managers. It's free to get started. Try it for yourself. Visit Mercury.com to learn more and apply online in minutes. Hello.

0:37Hey. How's it going? How's New York? It's good. I had the best time in San Francisco last week, and it was fun. It was fun to get to see you and Angela and Sally. So lots of pod love. And then I went to Miami for one day, and now I'm back. And actually, New York is no longer – it's like fake spring right now, which feels great because this has been the most brutal winter. oh man well it's it's very nice it's ever just go as you saw um and i think we're it's gonna be nice for a while which is fun okay so what did we miss we let's see things that happened that we were talking about brand is the moat i don't know if you've heard i i know paul graham wrote probably the definitive essay but i was so long like angela said she tapped out after like two paragraphs it was so long i actually i have to confess i did not read the whole thing it was yeah because it's too long i'm not gonna read it's not PR um but i do i do think like um i mean listen i'm a huge but we're both huge believers in brand and narrative yeah uh which is why i'm like this is fleeting this is so this is gonna be so short-lived like but you mean the sentiment or actually the value?

1:57The sentiment. Yeah. I think brand matters in a steady, always on way, always just like never more or less in any period. And also we work in tech where literally like the product is the most exciting thing because it's tech, like it's, you know, but I think right now we're just seeing this like flood of essays and think pieces about brand and taste. And I'm like, no, but I mean, I love it. It feels good. I'm reading everything and it's like the vibes are great, but I just don't know. I just don't think it'll last, but maybe I don't have a hot take. I think it is both like a fleeting sentiment, like it's like a hot take right now, but also maybe fleeting in terms of how, you know, like brand has always been considered the weakest of all the moats.

2:47It is a moat, like in the sort of classic definition of moats, but it's, And you can see it in companies like Nike or whatever. But in tech, brand has been eclipsed by things like network effects or switching costs or proprietary data, things that tend to be more tangible and enduring and things that might be on investor check. Measurable. I think measurable, right? Because I think tech, something's fast, okay, well then you can come up with something that's a little bit faster. Right. Or it's like there are these like performance metrics in tech and then other other industries where like, you know, automotive, for example.

3:29Right. Like in like the sort of luxury racing car space, like there's like you can you can sort of outperform. But brand is just so it's so squishy and it's just so like it's like the antithesis of like why people get into tech and like what draws people to step. It's masculine. We're shadowing the conversation we're about to have. But I guess the point I want to make is I think the reason everyone's like hot on brand right now, and it's the same reason they're hot on storytelling, is because we are in this moment where the classic network effects are harder to see in today's business, even the ones that are growing really quickly, right?

4:05So like network effects, like most AI products are still single player mode. Switching costs, like I don't know. I think a lot of, we talked last week about how Cursor and Cloud Code are not zero sum. And actually there are a lot of people who are using both right now and maybe trying like two or three other products in that category. Very unclear who's going to, I mean, okay, actually that's a good, that reminds me, Microsoft has entered the chat, right? They announced that they're like rolling out basically like AI native capabilities and like maybe some magenta stuff, like with Claude as the back, you know, backbone for it across all of Microsoft 365.

4:46And like, I mean, I'm personally somebody who thinks that like Microsoft is actually going to be the company that delivers sort of AI into the workforce, you know, into everybody who's already like living and breathing in the office suite. And I know that's such like an impossible narrative for us in Silicon Valley. It was like, who used Microsoft Word? I'm like, no, literally everybody. Like, guess what? People don't use Notion to like start a doc. And so I think watching them is going to be really interesting. Also shocking that they're using Anthropic, right? Not OpenAI, where they've got like a huge stake.

5:21It's fascinating on that level. And also because, you know, Anthropic is at war with the Department of War. And so any big announcement, like, you know, even though this has nothing to do with that, with Anthropic right now kind of feels like it carries more meaning. and more successful. And so this will be really, I mean, Microsoft has, you know, a long history of successfully bundling lots of things and therefore sort of like edging out the more like point solution tools. And so we'll see if they're capable with this. I'm just a little skeptical because Copilot was like very, very early to the market and it was kind of like theirs to win.

6:05And I think the prevailing narrative - But the tech wasn't there. The rollout was there, but the engagement and the adoption wasn't. But also, I don't think the tech was there yet, right? Yeah. I mean, the tech has gotten so much better. So this is definitely a huge distribution advantage because tons of people use Microsoft products who are not actively searching maybe for AI products, but now we'll have one at their fingertips. People joke about Clippy, and I'm like, no, it seems like a pretty good delivery mechanism. Yeah, yeah. Yeah, we'll all be putting a paper clip to usher us into this bold era.

6:41Well, you mentioned Anthropic. So yeah, they finalized or they formalized their lawsuit against the DOJ over the supply chain risk label. And I wondered two things. One, I think Anthropic was like a very hotly anticipated IPO this year. And I wonder how this throws a wrench into those plans, if at all. I don't know, probably, but I'm not sure. And then the other one is we've talked about on this podcast, like those multi-layer SPVs. Are those SPV holders sweating at all that they're sort of in this mess and it's unclear what is going to happen next? Because I think, as we talked about last week or the week before, sort of like the positive vibes around Anthropik and it's sort of like their moment to win.

7:29These narratives shift all the time. And I feel like this weekend there was also kind of like a little bit of a narrative shift on like how genuine was Anthropik's sort of rationale around like, you know, having that spat with DOJ. Oh, I missed that chapter. But I will say that. Yeah, I mean, I just think the cynical voice has just got a little louder. Yeah, there's always like the backlash, the backlash, the backlash. So you're going to go through all the waves. I think the IPO question is super interesting because normally like a massive lawsuit is absolutely a reason not to go out and be public because it introduces so much risk.

8:06But interestingly, in this case, given what's at stake, the supply chain risk, the threat of nationalization more broadly looming for AI companies, I almost wonder if the move is to go public and add like an additional like, you know, oh, government, are you really going to nationalize something that's like owned by Americans? It's very easy to paint Silicon Valley and an Anthropics cap table in this like populist light. It's like a bunch of billionaires and, you know, and who cares about them? But if the Anthropics is like owned by the people, I wonder if that introduces an entirely new dynamic to those proceedings, if not from a legal perspective, from like a court of public opinion perspective.

8:45So, so we will, I think it was, yeah, I think it was you who made the point in the group chat about how like, usually like the biggest haters on, on, on Twitter would be, you know, like a certain cohort of people, but they all invested in Anthropics last round. So they're, they're very quiet right now. And maybe that was strategic, but it's, it seems odd almost like they're not throwing stones. Maybe this is a new playbook. Yeah. A lot of people who are quiet for a lot of different reasons right now. The people who would normally be like critiquing, anthropic, like being too woke. Also, I've really enjoyed – there's been a lot of commentary about how there's been no commentary from David Sachs about the war in Iran.

9:30Oh, yeah. If David Sachs were alive. Yeah, yeah, yeah, yeah. So it's just like people are paying attention and silence can be the loudest thing sometimes. So yeah, it's kind of fun to watch the show. Amazing. Okay, and then Clue Lee, Clue Lee update. I don't even know why we keep following this storyline, but I think Roy Lee just does an extraordinary job of continuing to try to be the main character. And he's almost like a Rorschach test at this point, right? Like how you view his actions, because people have such opposing views of whether his video the other day was good or bad. or whether he actually did commit securities fraud or not.

10:16And even coming that close to me is not great. One thing that I thought was, it feels very 2025. It feels almost out of place. He is single-handedly carrying this attention-maxing strategy that feels kind of outdated and out of place right now. But maybe that's just me. I don't know. Do you think it landed? I think you're right. Maybe just for context, if people aren't quite as disgustingly online as we are, he made a video in response to a story that TechCrunch did about him sort of finessing some of his revenue numbers. And that story itself came out of some, you know, online Twitter banter.

11:03But essentially Roy was like, oh, yeah, some random woman from TechCrunch called me up and I didn't even know what it was about. Actually, your PR person pitched us and blah, blah, blah. Exactly. And then he was like, oh, here's what it actually was. And it didn't match it. And people are like, yo, dude, you're potentially committing security or admitting to committing a securities fraud right now. You might want to be quiet. And so instead of being quiet, he like clapped back with this very, you know, aggressive video. And it got some of the normal responses, but I actually felt, Helen, a lot of people were like you and I, where we were just kind of like, yeah, we've seen this before.

11:37Like we're kind of – also it just feels like we have bigger fish to fry. I know. Like 996 is no longer interesting. Rage baiting is no longer interesting. Like, you know, I mean maybe an anthropic Pentagon slash like Iran war story. like, like files. It's just all been eclipsed by things with like much higher stakes. And so I think that's like, again, something I just thought of, like, as you were talking there is like, I think when you choose to be really public and you choose to be really loud and you have a large following, right, you're collecting large following, you have to bring them with you everywhere you go.

12:12So when you like sort of make these aggressive shifts in strategy, this is why early stage startups should not build in public, in my opinion, because you haven't figured shit out yet and you don't want to like be whipsawing everybody right it's like so if you're if you're quieter you can kind of make those little adjustments along the way without like you know sort of looking like you're flip-flopping or that you're you know sort of exhausting people and I think we're seeing that play out right now right yeah yeah yeah okay let's get over to our main topic that's a juicy one okay so last week I spoke at an international women's day event before meeting Ashley for dinner.

12:53And I walked between the two venues and I had such a flashback on how this day in March has changed throughout the years. Like, I don't know if you guys remember the Bain Crypto Fund launch on International Women's Day in like 2022. I do not. Do you remember that? It was basically like, it was like peak. It was, yeah. Because it was like peak of the times, right? Everybody hashtag International Women's Day. And then it was like announcing Bain Crypto Fund. And it was just like all dudes. And you know what? The funny thing is, if that happened today, people would even bat an eyelash. But it was like so of the environment that they just got called out and trolled like left and right for doing this on this particular day.

13:40And there were articles about it. They were apologetic. I think they made a big deal about like actually showcasing a couple of women who were on the team but just weren't part of the announcement. It was a mess. But I was thinking about how like that moment, you know, wouldn't have been a big deal today, but like how this has evolved this day over time. And then that also got me thinking, I think like, I think that there's a lot of positive intent on people wanting to know exactly, you know, how to, how to support women in the workplace. And it feels probably somewhat of like a moving target.

14:12On a personal level, not like as a broader judgment, like none of the International Women's Day stuff landed for me in this particular moment. I was invited, which I always love to get an invite, invite me to all your parties, to this New York Stock Exchange event with Paris Hilton and Gloria Steinem, truly an inspired combination. I was out of town, so I didn't go. I think it was last night. We're recording this on Tuesday, so Monday night or Monday evening. And they turned the New York Stock Exchange facade pink. Oh, no. It was very over the top, as you would imagine, like a Paris Hilton event to be.

14:57She was kind of the main person. I think she has some bigger initiative around supporting small businesses. So there were some like real teeth to it. But I was just... Please tell me that they launched a coin. No. I think she was like a crypto influencer. Yes. Okay. But I was like great for people who are into this, but wow, this so does not work for me and of this moment to me. And I think I was reflecting a little bit on – I don't know. I feel like I'm in a deeply pragmatic phase right now with like a tinge of cynicism. And I feel like the people who care are doing things but mostly doing them quietly.

15:40And I feel like a lot of people don't care right now. And that's very different than earlier in our careers, which we can get into because we're old and white. I mean, this will be cynical, but I feel like earlier in our careers, people talked about caring a whole lot but didn't actually care. I would rather know where people stand than have people sort of towing a party line and expressing solidarity but not having any real action behind it. So anyway, so that's where I am, cards on the table. And there are lots of amazing people who are doing things. But for the most part, we are in, to use Zuck's phrasing, like a masculine energy era of tech.

16:26And yes, the Bain crypto announcement would not, no one would have batted an eye if that happened today. And it happens pretty much every day in my feed, something like that. And it's just a fascinating reminder of how quickly context shifts. We could even look at the evolution of who our heroes were, right? And so I was at Facebook from 2008 to 13. Cheryl had just become COO. And I think for a lot of women that I worked with, spanning all generations, they had never worked for a woman that senior. She was next in line to the CEO, right? And that was a huge deal. I mean, at the time, if you had named other leaders, other female leaders in tech, it was like Meg Whitman, Carly Fiorina, the bench of, you know, like the RMC presidential candidates for some reason.

17:16But like the the at the time, like it was it was a really, really big deal. And so I think that, you know, as you do when there isn't like more representation, you sort of like pin and you put so much pressure on that one person who sits in that role. And so then Cheryl, when she spoke, she had to basically be representative of every working mother or every female leader. And like that wasn't fair to put on her. But it also wasn't fair for, I think, a bunch of women to think that they had to look at her and follow this one example of leadership, you know. And so, yeah, to be clear. Yeah, she did well with it.

17:55But I think that now, I mean, especially having lived through like the fall of Lean In and, you know, different girl boss eras, you know, you can kind of look back and see like, OK, yeah, I see how like that particular perspective wouldn't resonate in today's audience. And so it's just been it's just been interesting how our heroes change. And I think I mentioned this in the group chat, but it's like I asked, you know, the young women that I work with here and some other folks, like who who is like I was trying to forget it. Like, who is the Sheryl Sandberg of your era? And like nobody had any answers for me.

18:29They had answers like, well, when I was in college, I really looked up to these women who are like in the girl boss set. But like now I don't I don't really know. And I think that's an interesting thing to talk about, too, because, you know, I think, does that mean that everybody is finding their own or are they their own, you know, hero? Women, pragmatically, is one of those things where sometimes what's good for the group is bad for the individual and vice versa, are keeping their heads down and not being super visible right now. And so there are so many impressive women in the tech industry right now who, like, have the substance to be that sort of hero status.

19:12And I think women have learned there is way more risks than a reward on an individual level to sort of taking on that mantle. I was just going to say that. They're all pretty quiet, right? Yeah. And listen, it makes sense on an individual level, but it's heartbreaking at an ecosystem level. and I think it makes it harder for any one person to stick their neck out when there's just so little visibility. But it's funny, you talk about Sheryl Sandberg. Like, it was so – and I was at Box at the time and I was very lucky. Like, Box was – I mean, it's funny, enterprise software founded by four guys.

19:46But it was just like a very – you know, it felt like a very, like, feminist or at least very inclusive culture. I had a female boss. There were lots of women in leadership positions at box. And so internally, I always felt, gender didn't feel like a thing to me. That was something to overcome. But I looked around the industry. Yeah. Well, and we can get into this later. Externally, absolutely. Because I think being in PR and comms, it was very gendered and came with a lot of assumptions at that time. And so externally, I felt it acutely. Internally, I felt very respected. But I do remember when Cheryl's book came, I read it as soon as I could get it.

20:29I actually was invited to do this TechCrunch video book club with a couple other investors. Like a Zoom book club before the Zoom era? No, it was just a video book club. A video recording of us talking about Lean It. And I was definitely the least impressive person there, which is always my goal in any room. And I haven't – I think they like maybe took the videos down or maybe I just couldn't find it quickly enough. But I am sure that I could have been canceled for things that I said because I think the beauty of LinkedIn and its fatal flaw was it was so focused on the individual. What are all the individual decisions you can make to further your career and your ambitions?

21:16And so like the advice is, you know, pick the right partner. And, you know, if you're going to have a baby, like don't lean out. And, you know, it was very much, it was very empowering in the sense of, yes, maybe the world is unfair, but here's a toolkit for you. And Helen, to your point about how, like, quickly things changed in the aftermath, I think we began to, like, face some of the systemic realities for women and other underrepresented people. And Lean In just did not have any sort of real answer for that. I also want to acknowledge because we do put so much pressure on our heroes. And you're right.

21:56Like that was a lot for Cheryl to carry. And then the world changed so quickly in 2016 with the election of Donald Trump. And I remember people being furious. Like Cheryl didn't have anything to say around the time of the Women's March, right? Like she was like the spokesperson for women. Yeah. How could she not show up in that moment? I think she had just lost her husband. So it was just like we can't pick individuals and expect them to be all things to all people at all moments. But the challenge has always been that there are just so few women who reach those heights. Right, right. And they have pressure on them that no man comes close to having.

22:37And this is a hard thing to solve because the only way to solve it is to get lots of people in positions of power. and so that you have a variety to choose from right you can like pick your flavor yeah you're speaking for themselves and their experience maybe like their company or their industry but um this could be a good transition to the girl boss era i feel like we went from the lean-in era to the girl boss era that's right that's right i mean that that actually resonates with me so much because I worked at Cora during the 2016 election. And I remember it was like this, you know, Cora at the time, like right outside the Stanford campus, a lot of folks we got in non-technical roles were like Stanford students who wanted to take a couple of years off before going to law school.

23:26And so, you know, maybe they were inclined in a certain, you know, sort of ideology, but like a lot of those were women and a lot of them were on my team. And I just remember like, oh, these women do not look at Sheryl Sandberg the same way that I did. and who did they look up to? It was a lot of like the girl bosses at the time. And I was like, oh, interesting. Okay. I think the girl boss label sort of gives me the, but like this is definitely resonating with young millennials. And I was like, okay, that's cool. And it was another like individual empowerment narrative. And it was so different.

24:02And it's funny, I inserted myself into this world a little bit when I joined Glossier in 2018. And, you know, there was this whole cohort of leaders. They were all building consumer companies. They were all incredibly media savvy and social media savvy. In fact, the rise of the girl bosses really coincided with the rise of Instagram. And so it was almost like there was a new platform for distribution of influence, and these women nailed it. And they were influencers and CEOs, which actually is a very tricky line to walk, as I saw firsthand with Emily. Like how do you get, you know, maybe you use your sort of influencer brand to build awareness for your company and your products, but then how do you transition to people taking you seriously as a CEO and business leader?

24:55But, you know, it felt like one magazine cover after the other, you know, Whitney Wolf heard from Bumble, Taylor from Outdoor Voices, Sophia, the original girl boss, and she coined the term from Nasty Gal, Audrey from The Wings, Steph Corey from Away. And media really like celebrated these women. I feel like, you know, these women were savvy, but also magazines and publications knew what people wanted and people wanted these stories and they wanted, you know, this was as much of like a lifestyle and individual brand as it was about the company brands. And so it was kind of a fascinating era. And in hindsight, it's obvious that that would topple at some point, because talk about putting people on pedestals.

25:44I think a lot of these women were sort of catapulted into, you know, the limelight earlier than maybe they otherwise would have been. I'm just given sort of the macro, the macro narrative and the excitement around, wow, look at all these, you know, eventually like billion dollar businesses founded by women. And it was exciting on the ride up. And then it was pretty devastating on the fall. I'm hopeful that what will emerge is, you know, women who have, you know, built really incredible businesses and, you know, done it their way. And, you know, I think there's like data, but there's a lot of anecdotes too.

26:20Like I think when, you know, female founders start companies, they just tend to attract, I think, more diverse leaders to actually like join the company. Like a great example is Christina Cassioppo at Vanta. Like I think her executive team is like half women and, and yeah. And like, she's not, I mean, she's out there, but I wouldn't say that she's out there trying to brand herself or do anything that we've seen in like these previous eras. And it's probably the right move, especially in the, you know, industry that she's building for. And I think, you know, the best thing that we can hope for is that Vanta is an enduring company and has like an incredible outcome.

26:59And there are a generation of young female builders who are like, oh, yeah, there's one. There's another way that you can do this. Right. And maybe that way resonates more with me. And so we just need to see more examples and they all need to not fit into like a like a cookie. I mean, the thing with the girl boss era was just like, you know, we tried to like paint them all as he's like glamorous. glamorous. Exactly. And, and, you know, I think people are multifaceted and people are, you know, very different. There are so many different styles of leadership when it comes to men. And there are, you know, so few when it comes to women.

27:35And so we just need more. And like, unfortunately, this is such like a devastating thing to say, but like, you know, like maybe we just need more time. I think that's all true with one caveat, which is that I agree that you don't have to be on magazines to build a massively important business. But for people who have the aptitude to be more public-facing, to not use, like, every tool at your disposal when building an iconic company is so hard does make me really sad. Like, you know, not every woman should put themselves out there in a super public way. But there are some who are uniquely adept at doing it.