The TPF Q&A: Casey Lewis, After School

Everything you ever wanted to know about kids these days.

Everything I know about Gen Z, I learned from Casey Lewis. She writes the exceptional After School newsletter, a daily compendium of all the things the kids are doing as well as a weekend edition for deep thoughts.

We talked about pivoting from Teen Vogue to TikTok, the business of newsletters, and how viral videos juice subscription numbers.

Casey, obviously. ©Courtney Lindberg Photography

Three Point Four Media: Was Gen Z whisperer always your professional goal?

Casey Lewis: I grew up obsessed with trends without knowing that I was obsessed with trends. I was just a teenager in Missouri who wanted to know what was cool. In college, I interned at Teen Vogue, and I also worked at youth consultancy YPulse. (It still exists, but in a different form.) At that time, youth trends were millennial trends. I was, of course, a youth. My job was combing the internet and finding things that marketers might care about. An understanding of what people think and want is a throughline in my career. As I got older, I got less interested in trying to talk directly to young people because it became harder to authentically reach that audience. 

You become the Steve Buscemi character. As Gen Z ages, do you think you’ll stick with them or pivot to Gen Alpha? 

My real interest lies—and this is truly marketing speak—in youth trends. Young people are trying to figure out who they are. They're trying on different identities. They're exploring music. They're exploring personal style. They are figuring out what they think the world should look like. I’m much more interested in that age group, regardless of generation. The oldest Gen Zers are turning 28 this year. That is an important consumer base, but it’s less interesting to me. 

Fifteen years seems impossibly broad for a generation given the pace of today’s world.

I couldn't agree more. I think there are two cohorts within Gen Z. COVID fundamentally shaped elder Gen Zers in a very different way than it did the younger ones. We’re going to see that dynamic with all future generations, too. Marketing to a 28-year-old versus a 14-year-old is completely different. Even the way the technology that both groups use shapes them is different. 

But also, Gen Z is now marketing shorthand for “young person.” A lot of times publications will throw Gen Z in a headline, like, “you'll never guess this crazy thing Gen Z is doing.” And the people quoted in the piece will all be 32 years old, which is literally not Gen Z. It's a weird, catch-all term.

Whenever I want to be dismissive of someone, I mutter “ugh, Gen Z” under my breath like a totally normal person. I feel like generations should be defined afterwards by specific events. Do you remember where you were when 9/11 happened? Or when Obama was elected? Trump in 2016 is probably another one. Your point about COVID, too. Those are much better dividing lines than these arbitrary year brackets.

Who knows what will happen with the TikTok ban. But if the app does go away, that would be a defining moment for this generation. Kids 10 and under, who are too young to be on TikTok, would be shaped totally differently than people only a few years older.

Okay, so pivoting a little bit: What do you do all day?

I truly do scroll all day. I spend a significant amount of time on TikTok. Last night, I went to a Substack party, and a girl asked me if I had read any good books. I had to flat-out tell her: No. In fact, I've never read fewer books than I did last year. I get so much from TikTok for my newsletter that anytime I have downtime, I feel that I need to be scrolling. The blessing and the curse of the internet is you can be a sponge and learn an infinite amount, even if what I'm learning is stuff on TikTok.

You probably read a lot of articles?

And newsletters. 

There you go. That counts as reading. You went full-time with After School about a year ago. How’s it going? 

I left my full-time job at the end of March. I had grown my paid subscriptions to a point where I felt like even if they didn’t increase I would be okay financially. As a highly anxious person, that peace of mind was extremely freeing but it’s also extremely scary to rely so much on one revenue stream. 

It's been interesting to have more time to think about the newsletter. I’ve been writing it for three and a half years, logging youth trends and societal shifts. I finally have time to look back at what has happened. I can think about it like a monthly trend report: What are the most important things that happened recently and how does that ladder up to what happened last month or a year ago? I can apply more of a macro lens. 

I've also started doing some corporate talks. It's very time consuming to put together these presentations, but it's been really fun. I'm already doing the research and so I can think, “Okay, what does a brand need to know from the last three to six months?”

I’m doing some sponsorships, too. I’ll be honest: I’m less excited about those because it’s less interesting. It’s so much back and forth to get a deal signed. But I have almost 65,000 free subscribers, and it feels silly not to take advantage sometimes. 

You’ve also been moderating panels. Do you like doing that type of thing?

I do. I'd been on panels before, but I'd never been the moderator until this year. It’s a little weird and nerve-wrecking, but you just ask questions. 

I’ve moderated a few panels, including one very surreal one at the Soho Apple store. Former U.S. goalkeeper Tim Howard had just released an app he knew nothing about and we talked about it with the very good natured app developers. All I could think was “How did I get here?” and “What is happening?” 

Did you get paid for that?

No! I think I should have! I’m sure the magazine that set the whole thing up did.

I don’t normally get paid, either. Just doing it for “the visibility.”

We need to break into a higher tier of moderatorship. Is your subscriber growth pretty steady or does it come in big bumps? 

There hasn't been any one big moment. When I'm quoted in a Wall Street Journal piece or something like that, I see a little bump. But a lot of publications don't link as a rule, so someone really has to Google or put in some effort to subscribe.

Last year I wrote a story for New York Magazine where I interviewed a bunch of tweens about style. They included the newsletter in my byline, and I saw some signups from that piece. Generally, anytime I can do a freelance piece that is impactful and is aligned with my subject matter, I see a bump. 

The weirdest and most surprising thing that I've learned is TikTok really does translate to newsletter signups. Doing front-facing camera work is out of my comfort zone. I don't love it, but if I feel like I have something to say, I can make myself do it. And it does pay off.

Has your ratio of free subs to paid subs stayed steady?

When I turned on paid subs just over two years ago, I had about 100. It's basically stayed around 5 percent of my free subscriber total this entire time. Substack tells you to expect a 10 percent conversion rate, which is not the case for me personally. But I also send four free newsletters a week and only one paid. I would be curious to know if people who put more of their content behind the paywall see higher conversion numbers.

Everyone I have ever talked to or read about has said that 10 percent number is fiction.

And subscription fatigue is real. I get that. Unless you need to know for your job or you have a real interest in what young consumers are doing, you're not going to pay me. That’s fine; no hard feelings. I read a ton of newsletters. There are a bunch that I pay for and there are a bunch that I don’t pay for. 

I would also think that it’s fine as long as the percentage stays relatively stable. You can plan for the future based on that stability.

And I'd rather have a high open rate on the free subscription because that feels like max visibility. I try not to get too sensitive about the paid numbers although there are times where I have felt it was going up so slowly. But at this point I'm pretty zen about the whole thing.