Full Transcript for Going Viral, Building Brands, and Betting on Founders with Ashley Mayer

spotlight. That's one reason why. So it's kind of hard to see when it pops up. I also see, I think more companies and organizations making unforced errors, maybe in part, due to the fact that the landscape is changing so rapidly, and there's so much I don't know there's the monoculture is dead. What appears to be a misstep to one audience might appear to be perfectly executed by another audience. So it is getting harder to say, well, that's that's a mistake, or that's a that's a great job done that. That being said, there are some things that jump out as great jobs. I will say just this week. Inc, so Airbnb relaunched its app this week to incorporate experiences and other stuff, besides places to sleep. Allison 7:28 Hadn't they been doing that for a while? Hani 7:30 Well, I just saw a wave of news coverage about it this week, and it was anchored, as far as I could see. It was anchored by a feature story in Wired, which feels like a tactic that you would see in 2000 by Steven Levy, by Steven Levy, right, who's one of the most well respected, well known writers, chroniclers of the tech industry. And to me that while it it felt tried and true, I think tried and true can be a really good thing, and it really anchored what it is they're trying to do, and the reasons why behind that, it's the lead tied into, you know, Brian Chesky, being very close with Altman from Open AI, and Altman being removed and then added back into his position. Allison 8:16 And I also saw they got a bunch of influencers too, like this very popular sort of millennial female influencer tanks went on and did some Airbnb experiences. So it did feel like they did a good job mixing the old with the new to some degree? Hani 8:30 I think they did exactly, yeah. They didn't throw out the old playbook, they adapted it and added some new chapters in. Allison 8:40 Yeah. So that's a winner. Hani 8:43 I think so. This week, that's one of the best things that I have seen this week. The other great thing that I saw this week, and this was to be expected, but the NFL, and I am a huge sports fan. 8:55 I am? What's your favorite? What are your favorite teams, Hani? 8:58 You know, it's funny you say that because at this point, I've dropped a lot of my teams in it. My son and I are both my son is 21 and he's a huge football and hockey fan, and we are both saying that we're Patriots fans, so we've seen enough Super Bowl with for the time being, but we're both saying that we are committing to traveling wherever the San Jose Sharks might be playing when they have a chance to win the Stanley Cup, finally. So that's the only team that we're really following anymore. Sean 09:24 So you’re going to be waiting a while. Allison 09: Meanwhile, I’m not sure I know what sports…. Play. Hani 09:32 And by the way, that team is loaded with a bunch of kids who are my kids age. They're like, 18,19, 20,21, it's frightening to watch. But what the NFL did this week in the midst of the NHL and NBA Playoffs happening, baseball is in full swing. The WNBA is starting this week, and WNBA is super hot right now. What the NFL did this week was something as boring as their schedule release for each team just. Keeps getting better and better. And I don't want to give the credit to the NFL. I think I have to give the credit to the individual teams. Because a couple of years ago, they really started to do these really interesting social videos around their schedule. Release the best one being when the Tennessee Titans in 2023 I can't really describe it, but go look—Tennessee Titans 2023 schedule release video. They put something up on Tiktok. Now has something like 6 million views, right? And it's fascinating. Basically, the NFL is eating everything in its path, and they have taken over the sports narrative, on social anyway, this week, while two other major leagues are going through some really great playoffs. So another good job by them. Allison 10:45 That's great. I mean, it is. It is sort of, though, when you mentioned NFL right now, to me, a logical segue into someone who's maybe not having such a good time right now. And despite my lack of interest in sports, I've been listening to some sports podcasts just to get a sense of what people are thinking about Bill Belichick and his relationship, slash work, co working situation with with his girlfriend, who's also his publicist, that doesn't seem to be going particularly well, from my perspective. Hani 11:14 It's watching a slow motion train wreck that then, you know, explodes into a ball of fire. I think, as I said, I'm a Patriots fan. I love Bill Belichick. I think he's probably somewhere close to a sociopath the way he dresses and his monomaniacal focus on—and please don't sue me Bill Belichick or UNC—but he is so monomaniacally focused on how he does his job, and that has worked for 20 something years, and this is the first major misstep that I've seen him just willingly fall into. Allison 11:53 Wasn't the cheating scandal sort of like the deflating thing? Deflate gates See, for someone who doesn't know about sports, they do know about controversy, but wasn't that another tough moment for him? Hani 12:02 It was tough for him, but at the same time, it was an us against them kind of outcome that made him even more popular. Sean 12:12 The Patriots fans weren't weren't thinking, oh man, what's wrong here? Hani 12:16 Everybody else hates Bill Belichick because they think he's a lunatic. I think a lot of that has to do with the jealousy over his over his six Super Bowl rings, and the success year after year that he was able to lead the Patriots to. But this has been a major misstep, and I think it's a great example of a couple of things, one being when you experience success for a long time, and every company has been through that. I was at eBay from 2003 to 2008. From 2003 to about 2006 eBay could do no wrong. We were coming out of the first tech recession. eBay was the one company that

really, really killed it during that time. Allison 12:55 Back when the US was really modern, yeah. Hani 12:59 Yeah, right. And then one quarter, eBay missed earnings by a couple pennies on the bottom line, I believe, and the bottom fell out of the reputation, and I was on both sides of that. And when you're used to success for a long time, and you're used to people kissing your ass, frankly, it's hard when they stop doing that, and you're not quite sure. Yeah. And I think companies need to recognize that, especially now, the good times aren't always going to last. The bad times aren't always going to last either, but it's, you know, it's hard to see that when you're in the middle of it. But for Belichick, I mean, so many mistakes have been made so far that I I think it's a 50/50 shot whether he even makes it to week one with UNC’s football program Allison 13:41 I heard they're bringing in someone more professional on the UNC side to take over there. But a couple of things have struck me about that situation. To your point, when you make a mistake like Deflategate, you're communicating to your core audience of Patriots fans who don't care. There's this quote I always go back to that I think really encompasses something you were talking about earlier as well, which is, no matter what you do, 1/3 of people will love it, 1/3 of people will hate it, and 1/3 of people won't care. So focus on the people who love it. And it seems like that's something that has worked for him in the past, but in this situation, isn't going to work again. Hani 14:16 He has, like, no natural constituency right now. Sean 14:20 Yeah, he does, right and Patriots fans don't care about him anymore. Allison 14:21 The other observation I had was, you know, that's more macro than just Bill Belichick, is there is this persistent perception of comms that if you find someone you know, sort of canny and good at getting attention, no matter how little experience they have, just just throw them into this profession, how hard could it be? And I listened to a couple of sports podcasts—extremely out of character for me—and that perception was on full display where people are going, Oh, she's just, he's just using her as some kind of a flack or whatever anybody can do that job being the underlying sentiment. And I really think that goes against everything we're trying to do in this podcast. So it felt important to talk about, well. Hani 15:00 We all, I'm sure all three of us, and everyone who's listening who has worked in this industry has felt that at one point or another where someone who knows nothing about comms strategy thinks that it's really easy to do the irony is that there are, frankly, a lot of comms people out there, including Belichick girlfriend, who think they know how to do it. Who can't? It's a it's a very, very hard job to do because it's more art than science, but there's a little bit of both involved. Sean 15:28 Awesome. Hani, thanks so much. Hani will be a regular guest on Attention Shift. We look forward to the live takes from Behind the Buzz, behind the mind of Hani Durzey on the show in future episodes. So thanks so much, Hani. Allison 15:44 Thank you, Hani. Hani 15:45 I appreciate you guys having me on, looking forward to the next time. Sean 15:47 All right, now we'll hear from Ashley on how comms fits into our investment strategy, what she learned from IPO comms and how a lost air pod landed her on national TV. Let's go. All right, Ash, you have, I think, forged a path of being out there talking about kinds of trends in communications as a communication leader. You have kind of taken aside the kind of this weird thing that communicators have where I have to be behind the person, I shouldn't be the one who's seen, I can't be, you know, out there, and you've turned that upside down in a really effective way. And now you're in venture, and you're investing, and you're still doing it, and you're also still talking about communications, in addition to talking about founders and the venture world. And I guess, like just to start, how has this helped you? And why are you keeping on doing it and now doubling down with a podcast? Ashley 16:44 Well, thank you. You make me sound so strategic when the reality was that, at least at the beginning, it wasn't. I remember when Twitter sort of came on the scene. Of course, Sean, you were there at the time, pretty early on, and when I joined Box in 2009 my CEO, Aaron, had Twitter account, but wasn't really tweeting. And I was like, you know, I think, I think CEOs are going to need to be more active. This is a platform. And actually, it was an especially good platform. Media were on Twitter in droves. Of course, that's less the case today given the current vibes on Twitter. So I was basically bullying him to be more active on Twitter, but it didn't feel fair to do that and not sort of understand how the platform worked myself. And so I got my start with Twitter and putting my ideas out there. Just because I was experimenting with it. I was having fun with it. Aaron was having fun with it. I was lucky that I got to sort of build up a Twitter presence before anyone was really paying attention or cared what I had to say. It's very experimental. It was very silly at the early days, but then over time, I realized what a powerful tool, it was. And again, at Box, my role was communications. And we were a very sort of media heavy, PR heavy company where that was sort of how we built our brand and awareness, and not just about Box, but the shift to cloud and SaaS and mobile. And so I was like, oh, journalists are here all the time. This is a great place to, like, know what they're thinking. And, you know, if I can get them to follow me and follow Aaron, even if we're not talking about Box stuff, we're going to be top of mind. And so it was just that, like, very simple insight around just like being visible, being top of mind. You know, as things get noisier,

there's there's real value there. And then I don't know, I've just always loved, like putting little ideas out into the world and seeing if they resonate, seeing what people think and Twitter was magical for that. Now, of course, today, we're in a different era, right where everyone's building personal brands and has content strategies and thought leadership strategies. It's a lot noisier, it's maybe a little harder to differentiate, I think, like, just participating alone doesn't, doesn't do so much. And so it's really maybe more about, like, the kinds of ideas and thinking that you're putting out there and what audience you're trying to connect with. There's a lot more, a lot more strategy behind it today, a lot more intentionality behind it today, but maybe also less leverage, because things are so noisy. But you know, I still love it. It's been fun to take expand into new formats, like you guys are with this podcast as well. Sean 19:26 So, I mean, I guess, like, as someone who's been had a personal brand before there was personal brands, what is the zenith of your Twitter career? Like, what's the one moment where you're like, holy moly, this is ridiculous. And then can that be repeated today? Ashley 19:42 Well, my brain went to my AirPod-Subway Rescue. Allison 19:47 My all time favorite, Ashley. I followed that like it was Severance, you know. Ashley 19:54 Oh my gosh. Allison 20:55 Each episode. What was gonna happen? It had us on the edge of our seats. Ashley 20:57 I mean, I was on the edge of my seat. I didn't know how that was gonna turn out. So I guess just the recap, the recap. So I had recently moved to New York from San Francisco, and the funny thing was, I was working at Glossier, which was an Instagram company, like, literally, no one at the company was on Twitter. No one at Glossier had any idea that any of this happened, because it was not happening on Instagram. But I, one day, was coming home from work, and I, like, stepped off the subway onto the platform, one of my AirPods fell out and, like, bounced a little bit and then fell into the tracks. And so sad. But I also was like, well, you know, what can you do? I went up to the little info booth, and they were like, well, maybe in three hours someone could come, but you have to stay here. And I was just like, you know what, it’s just not meant to be. The next day, when I got home from work, the AirPod was still there, and for some reason, that just made me feel so sad for it like, like, oh. Allison 20:52 It’s like a lost twin down there. Ashley 20:52 Yeah, it spent the night on the subway tracks with like, rats running around and, like, scary, noises. And I was just like, You know what I like, I'm gonna rescue that. And so right next to my subway station, there was a grocery store, and I went, and I just, like, bought, like, a hodgepodge of things. I bought a broom, I bought some duct tape, I bought some chewing gum, like, I had some, like, loose ideas of what

I what I might need. And all along I'm tweeting, right? So when I saw the AirPod, I was like, Oh my God. I had tweeted the day before that. I, like, lost the AirPod. But don't worry, I didn't, like, I'm not the first subway AirPod death and and then, you know, when I saw it again, I was like, Guys, he's still down there. And then when I decided to rescue it, I like, tweeted from the grocery store. Anyways, I tweeted my way through the rescue, which did ultimately work with some duct tape on the end of this broomstick. And then I, like, all the way through to, like, cleaning it and charging it and putting it back in my ear, which, like, horrified so many people. And you know, there was like, there were people following along, but, you know, not anything like insane. And then I woke up, and it was on Good Morning America, and it had gone viral overnight, and it was just such a funny like, you know, it was this can't be replicated Sean, because, like, it wasn't strategic. And I was just amused. It was like a delightful Twitter moment. And I'm still like the AirPod subway rescue girl through a bunch of people. And in fact, anytime someone like drops an AirPod down a drain, I get tagged in. Allison 22:21 What should we do? Comms, advice and lost items. Sean 22:25 I feel like, if it happened today, it would be someone would do, like a) LinkedIn post about, like the top 15 things I've learned about enterprise, SaaS sales, after dropping my AirPods. Ashley 22:36 And then, and then threads would find out about it, like two weeks later. Allison 22:41 Yeah, and be offended about some aspect of it. Yeah. Ashley 22:44 I don't even know what blue sky would think, but yeah, I think like, if there's any lesson from this, and also, like, my experience with Twitter generally, it's like, just like, be human, be yourself. I don't know. I feel like everyone's like, trying so hard these days, there's all this ChatGPT generated content, and I just don't know if that stuff like breaks through. And so I think people who know me know that I'm the same person online as I am in person, and it's a mix of like, silly things and burgers and dogs, but also, like, lots of thoughts about communications and tech. And, you know, I feel like the word authenticity gets used and abused so much, but I really do think that's the core of it, and so I'll try to not veer from that as I get older. Sean 23:28 You've worked with the B2B side to work on the venture. Worked at a venture firm before, in comms and marketing, and then you worked, obviously at Glossier, which is very much a consumer like you said, the Instagram company, a lot of different experiences. Now you're investing, you know, you have all these startups are looking to you for your insights, and, oh, my God, you have so many followers on X, and you've done all these things, like, in your, you know, it's just as simple as authenticity, right? So what are you giving them advice on? Like, what's the number one

piece of advice you give these founders as they're looking to… Allison 24:01 And how are you assessing them, too? I feel like there's just founders, at least working on the VC side. On my end, come in with such different levels of skill in this department, and do you only want to work with the ones who are innately good at this, or are you willing to take the hard cases? Ashley 24:16 Yeah? Yeah. I mean, I don't care if founder has like, a Twitter following, or is like, amazing on Broadcast. I mean, I do care about the story itself, and like the quality of the story and how much, like, you know, they, as a founder, are connected to that that piece is so important and and the story can be a little rough around the edges, but like, early stage startups, and I'm, you know, investing pre-seed, seed are mostly stories about what the future might become. And so a founder's ability to tell that in a way that, you know, gets investors to invest, early employees to join, first customers, to sign up, is, like, pretty existential. And so I'm definitely looking for like, is there like, a resonance story about, like, why this company needs to exist, and do I think this founder is someone who can tell that story in a way that can attract that sort of early attention and translate that into momentum? It's funny. I'm not like giving my portfolio founders workshops on like how to go viral on Twitter or anything like that. I think it's so individual. And actually, ironically, maybe more often than not, I'm advising them not to spend all their time tweeting or, you know, trying to, trying to build a brand, especially in the early days. I think that comms very much is tied to be in service of business goals. And so I oftentimes, once they get really crisp on what the business goals are, it's rarely like, okay, well, now you need to start a podcast. Like, I think there's, I think there's a lot that people do because they feel like there's some box to check and really, and you know, Allison, I'm sure you do this with your the founders and fans portfolio all the time. Like, like, you know. Someone comes to you, like, I want an article in Tech Crunch, and you have to sort of, like, take a few steps back and be like, Okay, well, well, let's, let's, yeah, like, what's your goal? Like, who's the desired audience? Like, what do you want them to do? And oftentimes, you know, you go down that path, and sometimes that leads in a very different direction of what the the fastest way to that is. And then, of course, there's the reality of like, you know, I think it's getting harder and harder to get press coverage. Like, the startup ecosystem is massive, and media, if anything, has, or at least traditional media, has, shrunk. And so there's also sort of the pragmatic piece of like, is this story worthy of, you know, worthy of coverage at this moment, or do we need to hit a bigger milestone? So I spend a lot of time with my founders, helping them figure those things out, or helping them figure out how to tell their stories in a way that will, like, break through the noise, or connect to some of those, like, 30,000 foot view themes that everyone's already talking about, so it's really resonant. But yeah, I don't think everyone needs a big personal. Allison 27:04 And I listen to Great Chat this week, which was a fabulous episode, by the way, and you talked a little bit about sort of the new communication strategy that you see someone like a Brian Johnson or, you know what, regardless of what you think about him. What you end up there with is, are these built in defenders that just don't care about a New York Times hit piece as you articulated, how much, how attainable Do you think that is for for founders, that type of, sort of cult, cult strategy, where you build a following in that way? Ashley 27:33 Yeah, I think, I think it's unattainable for most. You know, I think a lot of what is preached at founders is applicable to very few. Right? The whole go direct mantra, there's a lot of value in going direct everyone, if you can, should have, like, direct channels to your most important audience, the ability to speak to them. That's like, really, really hard to build. And so for most people, you need to be a little bit more scrappier and multifaceted than that. You can't just be Ryan Peterson of Flux Board and tweet about supply chain and, you know, and you're a hero of that category. That takes a lot of work and a lot of time. So, yeah, I mean, Brian Johnson is interesting, and, you know, I put him in a similar book, and his Elon Musk, which actually, I'm sure he'd love, where these are people who've already built. Their personal brands themselves are controversial and kind of chaotic and antagonistic, and so what someone can get away with when that is already sort of the expectation of their audience is so different, right? And I worry that, I worry that some of us are learning the wrong lessons from some of the most visible people in this industry. Because, you know, Brian Johnson. So there was, you know, there was a New York Times article earlier this year about his NDA practices at his company, Blueprint, and he definitely turned it into an interrogation of a relationship with an ex. It was only a tiny part of the story, but I think, you know, he sort of drew the attention elsewhere. But he is a person who benefits from drama and even negative attention, right? Like he, if you follow him on on Instagram or any of his channels, it's like, you know, he's calling himself a cult leader. And so someone like that just actually has like, a lot more freedom and how they and how they communicate and build a brand than someone who has a brand that's really built around, like, trust. And so there's just, like, a lot of self awareness that is, like, required when you're thinking about the tactics that you can use. Sean 29:38 Ashley, are you? Are you finding that founders are like hearing, kind of, I've heard about this

go direct thing, or I see, you know, these people giving the finger to the New York Times and using controversy as a way to get attention. Are people actually like trying to mimic that, or wanting to mimic that, or asking how they can get it? Because, like, obviously, we lived through an era for a long time where everyone's like, I want, some wanted to be Steve Jobs, right? And everyone's like, Can we do the Apple thing? Like, no, you can't do the apple thing because you're not Apple and you're not Steve Jobs, right? But, like, for a long time that was, like, the genius thing a CEO says, like, let's be more like Apple. And then you're like, okay, let's let's not, yeah, and, but are you? But I guess, like, you know, I worry about people kind of thinking that they can do that too, or it's so simple, or it's so easy, but I may be overreacting too, and I think there may be, is maybe some common sense from founders that you know, who are just saying, Yeah, I guess I'm not. That doesn't make sense. Ashley 30:35 I will say, I haven't had any found bearers who are like, helped me become the next Brian Johnson or Elon Musk, like on, you know, on these channels. I think they're, I think, you know, those are some pretty extreme examples. And I, I work with early stage founders, and so they're like, pretty heads down, building most of the time. The Steve Jobs comment is interesting, because we. We there was broad consensus that, like, Steve Jobs was an admirable leader, right? Maybe, like, personality wise, sometimes a little controversial, but like, the entire tech industry looked up to Steve Jobs, at least in his like, sort of comeback era, right? And like, releasing the iPhone and, oh my gosh, like, like, the adulation was off the charts. We live in a very different time now. I do not think there is consensus in tech, or even more broadly, on like, who our heroes and villains are. We are in like, I think it's like an anti hero era where we have these really complex figures who have things that are both admirable about them and also incredibly questionable. And I think tech is in this period of like moral ambiguity, like we were sort of like delayed or suspended morality. Like, if you think about someone like Sam Altman, his legacy is tied to how this sort of AI arms race goes. And you know, is Open AI going to usher in an era of human flourishing unlike anything we've ever imagined. Or, you know, will the doomers be right? Or will Elon Musk and Doge actually accomplish some things that are hard but end up being good? Or are they going to break everything and, like, I think there's, I think very few people, if we're being honest, like, know how these stories are going to end. And so it's actually like, very and I don't think even Sam and Elon know how these things are going to end. And so I think it's, um, I think everyone is kind of having to figure things out for themselves, which in some ways, is great. There isn't, like, a playbook to follow right now. There isn't consensus on what great looks like, or what leadership looks like. It's very fractured. It's very tribal. But on the bright side, I think a lot of us are having to sort of really reckon with these bigger questions ourselves versus like, you know, follow the playbooks or the blueprints from, you know, from the broadly admired leaders. Allison 33:02 Yeah, there's this old quote about art that whatever you create, 1/3 of people will love it, 1/3 of people will hate it, and 1/3 of people won't care. And I feel like in the current moment, we're saying all attention is good attention. Focus only on the third of people who care and forget everybody else. But I worry, to your point about tech’s reputation. Will there come a day of reckoning when we wish we had courted the people who are neutral or angry. Ashley 33:29 Totally. I mean, I like as an investor, I have to think about long time horizons, right? If I'm investing today, the environment those companies will exit into is like, many years into the future. And so, you know, great, maybe the Trump administration is going to be favorable in some ways, on some fronts, but like, the actually, like, what matters more is what's going to happen after this administration in many ways. And I think, I don't think there's, there are a lot of people thinking about, like, tax relationship long term right now and and that's fascinating to me, because it feels so obvious that that AI, even if we don't know, you know when AGI or even like super intelligence, but even if we don't know when that's coming, we can already see how AI is going to be very like disruptive to labor markets, and it's going to change a lot about how we all live in the world, and I think we're all just so high on, like, the progress and like, telling such a insular story to ourselves. And I don't see anyone thinking about, how do we tell a story to a broader, a broader audience and to the world, about like, what, what might be coming, and, and sort of, why this, why this is a good thing, um, and, and that's just, you know, that's a little scary, because things are moving at like, breakneck speed. Sean 34:53 I mean, it's really, I think it's, it gets back to the Steve Jobs thing. Because, like, again, you said, like, you know, Steve Jobs, you could argue on a lot of things, like what he did well and maybe things he did less well, but he did obviously build a great company, and beyond that, he did also articulate what the future looked like. And so people looked to Steve Jobs, and they said, Okay, well, he's really pointing towards something. It's out there a few years, and we're evolving on that place. And that's kind of the story he especially took along with the iPhone, among other things. That's the thing I feel like we're lacking the most right now to your point, and is impacting us the tech industry. Reputationally, it's like it literally is a new thing every day, like new piece of noise. It's just, I mean, it's

our entire media culture right now, but I don't know what it all adds up to anymore. I feel like I, that's been my job in my entire career, is like connecting these dots and telling the story of tech and telling where things go, go towards. And I've never been more lost. Ashley 35:55 Yeah. I mean, I think part of the challenge is no one knows exactly what's coming next, right? I think the pace of innovation is faster than most people expected, and a lot of what's happening, you know, if you talk to people who work in these AI research labs and these LLMs, like, like, roadmaps are changing in real time, because things they didn't think would be possible are possible. And so, like, the future is being written and rewritten on a pretty rapid pace. And so I think it is harder, it's harder to, like, help people understand what's coming when you only have sort of a fuzzy idea of what's coming. And I think that's why we just anchor on to these sort of, like, big terms. I have multiple definitions, by the way, like AGI or super intelligence and, you know, have done a relatively poor job with explaining to people what that, actually meant. Allison 36:49 The other one is Magentic, that I feel like has been utilized down to nothing, yeah. So I love that discussion of, you know, AGI means 15 different things, the same way autonomy with vehicles means 50 different things, and it's been interesting to see how words can get diluted to your point, to where they mean, to where they mean nothing. Ashley 37:11 Yeah, totally. I'm glad my job isn't to know precisely what the future is, and just to find people who have really interesting visions for slices of it and to make bets on them. I also think it's an incredibly exciting time, like, like, you know, how lucky are we to be in this industry that, as you know, we have a front row seat to whatever is coming next and, and it really is, like, quite astonishing. But, yeah, I do feel this, like there's this huge vacuum of who is going to, sort of, like, talk us all through this, not just people in tech, but people beyond tech. Those leaders are missing for me, and I think it's a real opportunity. I just don't know who's gonna step up. Sean 37:55 Well, Ash, you are a partner at a VC fund and coalition operators, and so you're stepping up, right? But let's talk about like this transition from being a comms leader into venture. Ashley 38:10 Yeah. Allison 38:11 I think a lot of people really admire your career trajectory, and would love to know how they could do it. Ashley 38:17 Yeah. Sean 38:18 It seems really glamorous and easy. So tell us how easy it is. Ashley 38:22 I’m so grateful. I didn't know what I didn't know going in. I definitely didn't think it would be easy, but I did not know how hard the transition would be from comms to investing in a lot of that is actually psychological. And, you know, in comms, you have these, like, delicious instant feedback loops, right? Like, if there's a

launch, you know, if it went well, if there's a story, like, know if it's hitting right and if people are getting it, if you have a challenging internal announcement, you know, if it went well and was trust building or trust eroding. And venture, you know, the timelines are just really long and the feedback loops are really long, and so that part of the of the career pivot has been the hardest to just actually like, be comfortable with that and be so grateful to get to do this job and be along for the journey and and to make the best decisions possible, and to to celebrate, like, the milestones along the way across our portfolio, but to ultimately, know, like, you know, this is, well, we'll find out in 10 years how, how this all went. I will say, like, the honest story of my career is, it's just an example of how, like, so much, is timing and luck. And, you know, I didn't, I didn't. I wasn't someone who, when I was, you know, early in my PR career, was like, someday I want to have my own venture fund, and here are the steps I'm going to take. Like, quite the opposite. There was a lot of opportunism and doing things because they were fun, and those fun things leading to opportunities I would not have imagined for myself. I mean, just quick bio. I was at Box for six years from early days through IPO, which was an incredible experience. I went into venture for the first time at Social Capital on the marketing side, so the marketing partner there, and so got that ecosystem view, got to work with early stage founders, and loved that work, but did not imagine myself crossing over to the investing side. And then when it was when I left Social Capital, went back into operating and led comms at Glossier that I started angel investing, and just really loved playing that role with founders. And both like supporting them, but also getting a deeper understanding of their business and being along for the highs and lows, and then the thing that really pushed me over into the path I'm on now was doing that alongside three friends who are now my partners at Coalition. And I think that the sort of magic of that partnership, the gratification of doing that work, alongside my day job. This was just sort of how I got my energy on the side. It was very organic. Like, you know, when I started angel investing with them, I did not think someday we will have a fund. Maybe they did, but I did not. And and then timing. So, you know, when I left Glossier, I still didn't know that I was going to be doing this full time, that I started spending more time across our, you know, our portfolio, and on the investing side, and then within the operator community we had built, and, like, started thinking, maybe this could actually be like a really differentiated venture product, you know, with the idea that, like people with active, operating expertise are some of the most valuable people on early stage cap tables. And yet, most early stage cap tables we saw as investors didn't necessarily have, like, the most powerful network of people on them that that founder, you know, could have assembled for so many reasons, mostly because early stage investing is, like, very opaque and network driven, and a lot of founders don't know what they don't know about what kinds of expertise they'll need down the line. And this is where the luck piece comes in. I mean, we decided to raise Coalition Fund One like at the end of zerpie times. It was late 2021 early 2022 that was an era where there was a lot of enthusiasm for emerging fund managers, people with, like, interesting operating backgrounds, interesting networks, interesting early like Angel track records. If I were going out to raise a first fund today with the same set of expertise, I don't think I could get it done, right? So I think this is, tech is so like boom, bust, cyclical, highs, lows, and I think our timing was perfect. We were lucky to raise at a time when it was easy to raise, but then the market shifted so we didn't deploy a whole fund into a, you know, a zerpie inflated market, and we've had the opportunity to really, like, prove ourselves as a center investors and build a differentiated product, and, you know, sort of build out a firm. So I think there are infinite paths into, you know, any potential career. But my advice usually to people is, don't be too attached unless, unless you just know your like purpose in life is to do acts like, don't be too attached to a particular outcome, like be open to sort of opportunities that present themselves to you and curious. Because I think careers are exercises in discovery versus, you know, strategy and mine certainly is. Allison 43:35 And I love your experimentation mindset. What made you decide to experiment with a podcast and how did that come together? Ashley 43:42 Yeah, so, yeah, we launched Great Chat this year, and I have four amazing co hosts. We're all, you know, investors, operators, founders, my co host, Sally, worked in media previously, and it's sort of a weekly tech commentary podcast. And that also happened very organically, as as most things in my career seemed to. I was in San Francisco, and the five of us had a dinner, and it was just so fun. And we even joked with that dinner, you know, we were like, talking about tech topics and being like, feisty and spicy, and we were like, Should we have a podcast? And so after that dinner, we started a group chat, and it was called, not, not starting a podcast. And you know, it was like, our, our inside joke for a while, but then we we started talking about it more. And obviously there are a lot of podcasts out there, as you both know, but we realized there was some like, shocking white space in that there are very few women led podcasts, especially in the tech and business news commentary space. Allison 44:53 As evidence with this tech bro podcast network that, yeah, somebody’s in. Ashley 44:57 I kind of love it, that it's actually a technology brothers,

technology bros, like, it's, you know, it's, it's, it's, um, hiding in plain sight, um, yeah. And so we just thought, like, maybe, maybe this would be fun and fresh and different. And like, let's put something out there and see if there's an audience, as I have on this podcast lamented that, like some of the loudest voices in tech, maybe are not the ones that I wish were representing our industry, and not that I have any belief that, like, I will be that person, but, you know, like, be the change you wish to see in the world. And like I, you know, maybe this would be a fun thing to try and and certainly on a personal level, like I'm so much more comfortable in writing than speaking in video, and so felt like a good way to get outside my comfort zone and challenge myself, not not only to show up in a way that is not sort of aligned with my natural, more natural strengths, but also to push myself to think more deeply about topics that, you know, I'm like, scanning and maybe engaging with at a surface level on Twitter, where it's, you know, a couple 100 characters at a time, but, but, you know, if you have a weekly podcast like, you're gonna have to go deeper and and I think you have to force yourself to find depth these days, it's very easy to skim along the surface and context switch. And so this is like, my weekly reminder, like, hey, stop and think, like, like, really, like, really, digest this. The world is moving quickly. So many interesting things are happening. And so yeah, on a sort of personal note, it's my, it's my weekly accountability to do that. You know, beyond, beyond doing that in my day job as well. Allison 46:40 Sean and I are new here in podcast land. I haven't yet gotten the ironic Brooklyn mullet, but, you know, I'm told that's coming. But what can we learn from your podcast journey so far? What advice do you have for someone starting a podcast? There are a lot of them to your point. Ashley 46:56 There are a lot of them. I'll do a little name dropping, I’m good friends with Casey Newton of Platformer and Hard Fork, his New York Times podcast that he has with Kevin Roose. And he gave me some great advice when I was, you know, deciding if I wanted to do this and what it might look like. And it was just like, make sure you're having fun, because, you know, you're signing up to do something extra weekly, and also, like, give your audience time to build. It takes time, like, you know, just keep putting stuff out there. It's not going to be perfect. And so, you know, that was the advice that I really needed. You know, I will not say that our first episodes were, you know, so crisp and sharp and polished, but like we started putting things out there, and we've kind of let our audience find us, Sean 47:47 I really appreciate that perspective and as you look inward, or as you're like preparing for your your podcast, or as you're just like scrolling Instagram and enjoying your day, like we ask every guest, what is capturing your attention right now? Like, what is like? What's the thing that makes you like? Keep a longer gaze at your phone. Ashley 48:06 Oh, interesting. I feel like I'm trying to have more of my attention off my phone these days. Okay, well, I'm all nerd out for a bit. I mean, I'm obsessed with like, ChatGPT, and this week, the obsession is I am doing continuous glucose monitoring for the first time. I'm already like, an Aura. I'm like, I'm a secret longevity bro myself. Allison 48:32 But are you measuring your nighttime erection? Ashley 48:34 I keep getting really bad scores, and I can understand why I get it. And it's like the data is so interesting, right? Because, like, it's just like everyone's body is so different. We respond to different foods differently. And I like, and I'm like, sharing screenshots of my my the app I'm using. It's called Lingo. My Lingo data was, like, my Aura data with ChatGPT and like, I have like, a, like, a, the best doctor I've ever had, like, who has infinite patience for me. Like, it is so exciting to see every screenshot I send it, and to tell me how brilliant all my insights are, but we're really making progress. And I'm like, Oh, this is like, this is gonna save my marriage, because I go to Gabe one more time. Like, check this graph out. Like, you know, at a certain point there's a limit. And so I am, like, I really, on a personal level, I am like, so excited about this technology and the personalization that's possible and, you know, and, and I'm sure there's so many different applications and exciting for shopping too, but from like, a health perspective, as someone who already, like, loves going down these rabbit holes, and it's just such an incredible unlock. And I like, have never felt more like, like, I see people being like, oh, like, we're outsourcing our brains to chat GPT. And I feel so the opposite. I feel like, it's like expanding the surface area of what I can dig into. And now, so, um, so, yeah, so that's like, where I'm spending. I feel like, I feel like ChatGPT is probably if I looked like my my like number one app in terms of usage. So watch out, watch out Twitter, but much happier place than my Twitter feed. So. Allison 50:17 ChatGPT definitely knows now how to get AirPods out of the subway grate. Ashley 50:21 Yeah, yeah, Oh, totally. I had like, you know, I probably wouldn't have had to tweet my way through it. I would have had step-by-step instructions. Sean 50:28 Ash, thank you so much. Really appreciate it. Love seeing you. Love talking to you. Ashley 50:33 This is so fun. Congrats on the pod guys. Sean 50:36 All right. Appreciate it. Talk. Bye. Allison 50:38 Thanks, Ashley. Allison 50:42 Thank you for joining us today for Attention Shift for today's deep dive on communication strategy. Check out our sponsors, Delve, at Delve.news and Mike Worldwide at MW.com Please like and subscribe to attention shift on Apple, Spotify, or your podcast platform of choice, and we'll see you in a couple weeks for our next episode.