Casey Lewis: Creator of After School

21:15And that is kind of what it ended up being where we had all of these email subscribers, but it was nothing in the sort of realm of Viacom numbers.

21:24Casey Lewis:Got it. So at what point did you start thinking about leaving and going to New York Magazine? About a year in, I believe, we were commuting to Times Square. We were trying to pitch into different Viacom areas. We were just trying to make ourselves and our community useful. And then at one point, they cut us back from five newsletters a week to three. The bummer was Liza and I had less and less to do. And it was like we moved from a gorgeous office to literally the coat closet kind of thing. And we see where this is going, but we had contracts. Eventually, I was like, I'm such a fidgety person.

22:06I can't come to the office and just read the internet. I just can't keep doing this. And it felt like our hands were kind of tied. And so we both left. Then we had six months to sit and figure out what was next. next. And I think we both independently spiraled a bit during that time because we had had our sort of dream media careers. And then we had started this thing and it was such an exhilarating experience. And then it was like, what in the hell do we do next?

22:36Casey Lewis:Yeah. And it turns out that the answer to that is New York Magazine. Talk to me about that. Yeah, I kicked around some other startup ideas for a bit. I was really interested in this idea and still am, but like would never pursue it. I mean, it's really like what LTK is doing, just being able to see clothes on a variety of women and that kind of thing. But for teens, I was really interested in teen personal style, kind of kicked around a bunch of different teen youth culture adjacent ideas. And then I started talking to Alexis from New York Magazine about would they be interested in a teen style vertical or column or what that could look like.

23:18So I had a couple of great conversations with her and then ended up joining full-time right before the pandemic. How'd that go? Well, you know, it's funny because Alexis and I had talked about a lot of like cool teen ideas. You know, do we do prom or, you know, what kind of like personal style can we incorporate into the strategist in a way that would be cool and make sense? But then because of the pandemic, everyone went into absolute survival mode. And so, you know, I was editing articles about like the best vacuum if you have a dog. I think the world of New York Magazine, and I look at the strategist daily still, I'm so grateful for my year there because the editors are so talented.

24:00And it's, I believe, like one of the best print products out there. But after a year there of editing, it was just editing wasn't enough anymore.

24:08Casey Lewis:Well, you'd had like strategy and oversight. Right. I think there's something kind of weirdly freeing about it. And then you hit that point, and you're like, I've got more to do here. Yeah. And I think a lot of people went through a sort of identity crisis during the pandemic, being at home. And I was thinking, do I not want to work in media at all anymore? What is my path forward? I thought about going to get my master's of social work to work with teenage girls, but an MSW was not the right path for me. But I was just kind of grasping at what I should do instead and what would feel better than just editing because I still love media and I love writing, but it wasn't fulfilling anymore.

24:47And so I put in notice at New York Mag without really a plan. And in tandem with that, it's so weird. But I still had a month left and I thought, I am seeing so many TikTok teen trends pop up every day online. I'm trying to keep track of all this. It's so exciting with TikTok and the sort of velocity. And I thought, what if I did a daily newsletter that's for myself, but like keeping track of all of this? And so for the last month, I did the newsletter five days a week for myself. I didn't tell anybody. It was just like quietly there. So we're talking about your personal sub stack, which is called After School.

25:24Casey Lewis:Yeah. So you launched and created a full on secondary job while having a full time job that you ran simultaneously. Yeah. I mean, it was really a beta version because it was just more like, is this just a fleeting idea that I think will be fun? And so that's why I kind of wanted to like stress test it. It's so true. There's a difference between feeling passionately about something and having a full-time day job of doing it. And to your point, it's like, even though obviously this was your wheelhouse, you have to really stress test something and see it's like, is this a vibe? Is there enough here?

26:01Casey Lewis:Is there enough there there? Yeah, I felt like I need to sort of incubate this without any eyes and make sure that, you know, I'm not setting myself up to crash and burn. There's so much that I love about technology democratizing opportunities for folks. Now, if you have a microphone and an idea, you can have a podcast. If you can type something, you can have a sub stack. And I think it's wonderful that we have like more people entering spaces. But one thing I've really noticed is like, there's a big difference between thinking that you can do something and really like having the chops to do it.

26:35Casey Lewis:There are a million discarded podcasts because people start them and then realize it's hard. There are a million sub stacks that people start and then abandon because it's hard to have ideas, to keep going back, to continue to find something interesting, to say nothing of building all of the audience. That is a real skill set. And also like you're set up for it. This is your skill set. You are the sort of person who should be doing this, you know? Well, thank you. You know, it was a really fun month. And at the end of it, my job ended and I was like, I'm so excited to keep doing this. Got it. Okay.

27:08Casey Lewis:So talk to me a little bit about early days of after school and sort of like how it felt different from Clover and from your other work at Teen Vogue. And who were you writing for in the very beginning? I think I was really writing for myself. I know that sounds like naive or tripe. I built a whole business on it, honey. It's fine. Who What Wear does so much great trend reporting in a sea of fewer fashion publications these days. And anytime there is something new, novel, it tells us about the moment that we're in in society in one way or the other. And so I think when I'm reading a lot of this stuff, I'm trying to figure out why is this happening?

27:48What does this mean? What does it say about what's next? And so like 6 '7", for example, which is over.

27:55Casey Lewis:Not in my house. My second grader is still there. She's still at the restaurant. I think it's figuring out... Gen Alpha clearly feel like their parents know everything. They want to have a secret language. They want to signal to their peers that they get it and that they know what's happening. There's just a lot to unpack, I think, with so many of these trends, even the dumb ones. When I'm reading anything, or even a TikTok, if I see a TikTok, I want to understand why is this happening and what does it mean? And so as I'm reading these articles and putting together the newsletter, I'm thinking like, what is the insight here that maybe we want to like take forward or maybe is indicative of something more?

28:32And a lot of times it's not immediately clear. Although now having done the newsletter for five years, I'm very much starting to see more patterns of like, oh, this moment came from this thing that happened a couple of years ago. You can tie it all back together. Yeah. I'm constantly thinking like, what's the insight here? And so the audience really is, for me, the audience of one, but it resonates with marketers. It resonates with people, with kids. They just want to know what their kids are doing and saying teachers. It turns out a lot of people want to know what the kids these days are doing.

29:01Casey Lewis:I mean, I certainly do. I find it so fascinating. And also it's such a service because I spend too much time on TikTok already. I'm not going through every single haul and figuring out like what people are interested. I appreciate that you are this trusted resource who's actually doing the reporting. I think that's part of what I really respond to is like the reporting and the authority. And like you are watching a thousand back to school halls. You are coming up with real original data and packaging it in a thoughtful, interesting story. It's so fascinating. And you do such a great job of it.

29:41Casey Lewis:At what moment did you realize like, oh, this thing that I'm writing for myself has legs? I never needed to like really put pressure on myself to get the numbers up. And I was never planning to do like sponsorships or monetize it like that. I was just happy to write it. When I first started, I constantly was checking to see who was subscribing. And so quickly I was seeing, oh, people from Meta, people from Nike. It was like, okay, I have 8 ,000 subscribers or, you know, even fewer. But a lot of these people seem like they're making deals. And so that gave me a lot of early confidence in it. But still at that point, I didn't have enough subscribers to make a living.

30:20And I wasn't really getting tons of inbound for consulting. My husband and I had a lot of conversations actually where he was like, you're onto something. I believe in you. This is great. And I would say, you are my husband. You are biased. I'm just not making enough money here. That's the thing about building a, I think subscription media business is it really does take time. Now I am so happy with my paid subscribers. I'm so grateful to have what is essentially a monthly salary from them. But I mean, I'm five years in.

30:49Casey Lewis:So just to give people some context, like you can make money through affiliate links. So if you talk about a pair of jeans, you can link to that pair of jeans. And if someone goes and clicks on that link and buys the pair of jeans, the person who referred them gets$10. There can be branded content where you're like, this story is sponsored by so-and-so, or you can review something or you can create original content around that. Or there's the subscription model. And sometimes all three of these play together. Sometimes it's like there's a monthly subscription, but people still do branded content.

31:19Casey Lewis:They sometimes still have affiliate links. Now there are lots of purists who are saying, I'm not doing affiliate links anymore. I'm only doing subscriptions. And there are a million different combinations. So walk me through a little bit about how you thought through this piece of things and why you chose to do what you have done. Yeah. So I think about a year in is when I turned on the optional subscription. I turned that on just to kind of experiment. The Substack team at that point was kind of pushing people to try it. And so I thought, sure, I could use the money at this point. And let's be clear, the reason Substack was pushing people to do that is because that's how Substack makes money.

31:55Casey Lewis:Because Substack takes a percentage of that. So Substack was incentivized to make you and everyone else turn on subscriptions because they could make revenue that way. Extremely good point. I turned that on. And then at the time, I was also doing some monthly newsletters for a couple of different companies who are interested in youth culture. So they both came inbound from the newsletter and said, what can you do for us? One was a video game and one was sports. Interesting. And not that they were only interested in sports and video games, but anything that their marketing teams could use potentially as ideas.

32:28So I was doing those as well. Maybe it was biweekly, both of those.

32:32Casey Lewis:How did you think through how much you charged? You know, this was three summers ago, and I definitely undercharged them. And I was just happy to have a monthly retainer at that point. Okay. I was just trying to build up to what I made at New York Magazine. Just replace your salary. Exactly. And so I cobbled together, and I think I did some freelance writing as well. and then a VC reached out because they were looking for a content comms person. And it was at this point that my husband was like, I think you're really onto something here. But I was starting to ache for that stability or I just didn't feel like the newsletter subscription side was growing fast.

33:14And so it was a great VC, 776, Alexis Ohanian's firm. And so I took that job. They let me continue doing the newsletter. So that would have been a deal breaker if they hadn't. So once again, you had two jobs. I did. And it was honestly an insane year. I lasted a year there doing both. And by that point, the newsletter had grown such that I was like, I can't keep doing both and I don't need to anymore. It was an awesome experience. And I learned so much about VC investment, but too much is happening. And I remember CNBC invited me to come on to talk about trends or something. And it overlapped with a meeting that I was supposed to have internally.

33:53And I just thought, I'm passing up panels and things that I feel like would really help further the newsletter side of the business. And I think that it is time.

34:03Casey Lewis:Amazing. By the way, part of the reason why I do like going down these side roads is because I think it's really important to explain, like, it's not always just linear. You have to do other things on the side, get it to a point where it's paying for itself. And like, how do you weigh where your time is going? And the reality is, is that from the outside, we all just see this wildly successful product, but having to go back and forth and do all these different things, like as a business builds, I like hearing about that. And also the reality of it is that you're not just like funded by a wealthy partner.

34:38Casey Lewis:I mean, not that there's less work when that happens, but you're dealing with real world pressure. And I think that's more inspiring and important to talk about too. Totally. Okay. So now you are after school full time. Yes. What is your research process like today? And how is that different from five years ago or four years ago? I've now been all in on it for two years. And as the newsletter has gotten bigger and as it's become what someone might perceive to be more successful, it's become more of not a burden, but I take it like even more seriously. And so it takes me longer to send it every day because I'm like, is this the best word I could use here?

35:19And I don't know if that's good or bad, you know, because I also at heart am a writer. And so it's fun for me to tinker with words, but I can tinker with words forever.

35:29Casey Lewis:It's never done. That's the thing about writing. It's why when I'm stressed, I reorganize my closet to some degree. It has a finite beginning, middle and end. Writing does not have a finite end. Yeah. My research is pretty similar. I have all my go-to publications. I'm scanning headlines. I'm trying to look for anything. Obviously, that mentions Gen Z, teens, kids, social media. But then a lot of times, you have to just do the scrolling. There's no shortcut. And it's funny. When I first started doing the newsletter, I had like Google news alerts set and now Google news alerts are just absolutely unusable.

36:06So pretty quickly I had to like pivot. But yeah, I really relish though the research and I could probably make a lot more money if I outsourced some of it, but I don't want to because so much of what I'm doing here is for myself and like trying to be the most informed about this as possible. And it's for me a lot about making connections in my own brain. So like if I see a headline tomorrow about paddle being the next pickleball, I want to be able to think like, wait, did I not see a different Wall Street Journal piece a couple of months? Like I want to be able to like track those things myself.

36:42If I outsource really any step of it, I just think I lose that.

36:46Casey Lewis:I get it. Are there certain groups of teens that you find more useful wells for reporting? Are there pockets of like, oh, wow, like the Newport, California kids are always really on this trend or like there are three girls in Dallas who start something that then sweeps the South or like, how do you sort of filter? This is a meaningful signal from this teenager who has the juice to signal to other teenagers. I think that TikTok, it's a hugely valuable tool for me, even just with my FYP, because I strictly use TikTok for research. So my feed is like pretty much all teens. And sometimes I will like step out of that to research, you know, whatever trend or whatever.

37:32But with back to school, things like that, I'll go down lots of rabbit holes of, you know, back to school halls. And then like, oh, this girl also did a get ready with me video. She seems like she could be the coolest one in her friend group. So I do a lot of that kind of stuff. And obviously, TikTok is not an exhaustive platform when it comes to teens. But I do feel like people will see a lot of these teens. And then they also want the Samba Janes or whatever. And so I find that TikTok is just definitely the highest value platform for me. And I spend too much time on it. But last week, I was on a road trip with my husband.

38:10and I was not looking at TikTok. And I was like, I am missing so much research right now. I feel the memes passing me by.

38:17Casey Lewis:I'm not going to understand about what the Martin's hot dog roll means. Like all of a sudden you're not catching the reference and it feels yuck. Yeah. Professionally, I'm like, I really can't be seen not getting the thing. So that's probably the trickiest part of the job is finding any sort of balance because I love being around my friends and family so much. At the same time, I really do need to spend a lot of time daily scrolling. And so I figured out ways to do that in a healthy way, such as I have a walking pad. I feel like I have struck a semi-balance. How do you think about your own social media creation piece when it comes to after school?

38:57Casey Lewis:I see you on TikTok. I see you on Instagram. How do you think about those platforms for your personal business growth? growth? When I get busy, the social media stuff is the first thing to fault. The newsletter and scrolling, which feeds the newsletter, is for sure my biggest priority. Even when I'm super busy, those are non-negotiables for me. The social media stuff is a lot trickier to do because you need to form thoughts. You need to find a quiet room. You need to look camera ready. You need to edit. And for me, I'm a writer by nature. I just am not as comfortable doing that. I will kind of go through spurts.

39:36And if I really have something to say, then I'll be excited to make the TikTok. Otherwise, I kind of have to be like, okay, it's time I got to do this thing.

39:44Casey Lewis:Are there times when you're like, all right, well, I have certain tent poles I have. I've got back to school. I've got holiday. I've got like certain times when you're like, I need to carve out time because this will be when everyone's talking about X, Y, and Z. Exactly. A hundred percent that. It's the sort of downtime that I'm a little bit more like, if I have a take about something, I'm going to do it. But otherwise, I'm not going to make myself make a TikTok every day. I've tried that kind of stuff. It is a big burden on my brain. And so I just don't make myself do that. I would like to do more of it.

40:18It's been a couple of weeks and it's something I think about every day. I need to get back in the game. But part of my afterschool business is I do speaking at like off sites or things like that. So last week I was, you know, doing a presentation at the office from nine to five. And so I wrote the newsletter early in the morning and then I had to, you know, practice the presentation and then I went straight to the airport. But the nice thing about the newsletter is I can do it in my pajamas. And I suppose I could do a TikTok in my pajamas, but that's not.

40:50Casey Lewis:You're too millennial to do that. Exactly. I'm way too vain. So talk to me about the side business now and how all of that has evolved. What percentage of your income is newsletter versus like all of your additional consulting work and speaking engagements and all of that? So to even zoom back to the newsletter, it's probably a third subscriber, a third paid partnerships in the newsletter, which I don't do a ton of. And then speaking is probably a third as well. Like this one I did this week was you big company have been studying Gen Z for years, you know how old they are, you know those sort of broad strokes.

41:28Here's what is happening right now. Here's what's next. And here's what you should be thinking about Gen Alpha. A lot of it references back to the newsletter. Like every day I'm researching and researching and researching. So when this company reached out, it's like, okay, what has happened in the last three months that I feel like they should know? And so some of it is like the wellness starting headline last week. Like they're a company that would care about generally young people prioritizing wellness in different ways. And like, obviously, we've seen the headlines around run clubs for years, but like, this is still happening.

41:58And this is how it's evolved, you know, since you last had a temp check on this. So it's really fun. I'm not a natural born speaker, but it's been fun to kind of push myself into making presentations and talking about these things.

42:13Casey Lewis:That is so cool. I talk about this all the time at work. But diversified revenue, diversified content streams. That's where it's at because I went through that Facebook time too. When the spigot gets turned off, you still have other opportunities. I am sorry that your diversification has been born out of trauma, but I think you have built a really healthy and thoughtful business. And that makes me very excited for you from the outside. Thank you. What is the most rewarding part of creating After School? And also, are you still a one-man band? So I have a manager, Max, who's wonderful. Oh, Max.

42:48Casey Lewis:Max is amazing. And working with Max and his team, it's been about a year and a half. Basically, you know, he does like all the negotiation, like every bit of getting paid. He is so extraordinarily helpful. Even things like figuring out my flight and hotel. Those are things that add up and take up brain space. And so to have that side of the business dealt with by someone else has been just a total game changer. I can't tell you how much it's changed my day-to-day. If you count that, I'm still doing every bit of research writing, and I'm not interested in managing. I have been a mentor at times in my career.

43:24But at this point, I just so value being able to go down rabbit holes, write about what I want, and just really sit with all of this and think about it constantly. The most fulfilling thing truly is I wake up and I'm like, what am I going to learn today? What crazy thing is going to happen today? It's such a fun topic. And five years in, it's still just so fascinating.

43:47Casey Lewis:I love it. Okay, so we always like to wrap up this podcast with the same three questions. The first one is about mistakes because we all make them over the course of our career and we don't always talk about them. But I think it's really important for women to hear stories of failure or mistake and then resiliency that comes with it. and to say like, you can make a giant mistake and still come back from it. So can you tell me about a mistake that you've made at any point in your career and what you've learned from it? Yeah, especially now that I'm running this thing by myself, trying to figure out how to show up in this new media landscape, who are the right partners, how do you want to show up in the world?

44:30At what point is saying yes, putting yourself out there and pushing yourself versus how should you maybe interrogate partnerships a little bit more critically. And I think especially in this political landscape, it is extremely hard to figure out who the right people to align with are. So I have had some tricky learnings this last couple of years as a lot of times the people with money are the ones who are the most controversial. It's very, very tricky to figure out what is okay and what isn't. It's a fine line. At some point, you do have to take paychecks, but at some point, you also have to say no to paychecks.

45:09It's been very hard for me. I'm extremely trusting. So I'm like, they obviously have honest intentions. I think that's like the biggest thing, hardest thing that I've learned since doing this full time is just to sort of interrogate any partnership who you're aligning with a little bit deeper.

45:26Casey Lewis:I hear you. So a lot of the folks who listen to this podcast are in their first lives and they know they want to do something different. Sometimes that means moving industries entirely. Sometimes that means doing what you and I did, which is evolving within the same industry. But these people are scared. They're worried about making a change, of making a leap, whether that's going out on their own or just moving in some capacity. What advice would you give someone who's standing there thinking about making a move but just hasn't done it quite yet? I have had a lot of friends who have been kind of faithful worker bees, worked at their companies 10 years, which is sort of rare even for millennials, but in the past couple of years have decided to cut themselves loose to do the same skills, but be self-employed or do slight pivots.

46:16And I've never met someone who regretted making that decision. It always feels scary and like, you know, what if they won't hire me back? And I think that even though this is a very fraught job market, making a change that you've been thinking about is going to lead you to better things. At least in my experience and in my network, I've just never seen someone regret leaving a job that they felt unsatisfied by. And I know that, again, it's tricky in this job market, but I think that pushing yourself forward is not going to be something that you regret.

46:53Casey Lewis:Doing what you did, which is not exactly suggesting an easy path, but doing both until you see if the thing has legs, doing both until you see if you have the appetite for it personally. That is a very reasonable and qualified way of going about trying something. It's going to be more work than you could imagine, but at least it will give you a clear view of what the possibilities are. I mean, you didn't just jump. You were very thoughtful and worked really, really hard to get something off the ground before you made the big move. So, I mean, I think truthfully, look, I'm a Virgo, so I run practical, but I think there's a way that you can try it in a way that reduces harm potentially and also allows you to explore.

47:39That's a good asterisk to my thought, which I think is test the waters to the extent that you can. Yeah.

47:45Casey Lewis:Okay, so my last question is my favorite, which is if you could get into a time machine and go back in time and speak with your younger self and give younger Casey some advice, what would you say? I mean, it's just so crazy, Hilary, because if I was to go back to my high school self, like I'm living like exactly the life. Even though the internet and teen mags don't exist in the way that they really did back in the day, I would say just keep doing what you're doing. But it's also funny because the work that I'm doing day in, day out is not so different than me being 15, coming home, and doing my little writing for the day.

48:22Casey Lewis:But now you get paid, honey. So yeah, I would say just keep writing every day. That's the path to success. You're going to write yourself out of this. I love it. Well, Casey, congratulations on everything. It has been such a pleasure watching your career from afar for all of these years. I have been a fan of yours for ages and ages. And I personally am really looking forward to you creating a gift guide that I can use for shopping, for the kids in my life, for the holidays. So I'm just going to slide that over and just let you know that I'm expecting it. And I expect you to reap the rewards of that affiliate income.

49:01Casey Lewis:send it my way, please. Okay. It's coming. Okay, good. But thank you so much. This was such a treat. Thank you, Hillary. This was an honor.

49:16Casey Lewis:That was the creator of After School, Casey Lewis. For more inspiring interviews with women like Casey, head on over to secondlifepod.com, where we have so many more for you to peruse. If you like today's show, please subscribe on Apple Podcasts or Spotify or wherever you get your podcasts. And don't forget to rate and review us. We love seeing you spread the word on social. And now you can tag us in your posts. We are at Second Life Pod on Instagram, Twitter, and Facebook. We always want to know who you're interested in hearing from on the show. So send in your requests to hello at secondlifepod.com or you can DM us on Instagram.

49:55Casey Lewis:I'm at Hilary Kerr. The show is at Second Life Pod. Our DMs are always open. I'm Hilary Kerr, and you've been listening to Second Life. This episode was produced by Hilary Kerr, Summer Hammeris, and Natalie Thurman. Our production assistant is Grace Ingram. Our audio engineers are at Treehouse Recording in Los Angeles, California, and our music is by Jonathan Leahy. Thank you.