✌️ Leaving her day job for a newsletter (again)

A crucial difference between traditional journalists and creators is that journalists don’t own their audience. The outlet publishing their work acts as a middleman, giving them access to an audience while editing their work and paying a set fee.

Even freelance journalists (about a third of US journalists are freelance¹) who exclusively publish in traditional news outlets have crucial differences from creator-writers who primarily distribute their work in a newsletter they own — though both lack benefits like employer-sponsored healthcare.

Of course, plenty of journalists who have developed their own audience as independent creators still occasionally publish work in traditional outlets; there are nuances. Today’s guest is one of many forging this path.

— Francis Zierer, Editor

P.S. Don’t forget to fill out our usual poll at the bottom of the newsletter if you have feedback about this specific issue of Creator Spotlight.

Casey Lewis has been writing about and for teenagers since the moment she became one.

At 13, while exploring the web, Casey noticed that the teen section on fashion.about.com wasn’t updated as frequently as the rest of the site. So she contacted the editor, Cynthia Nellis, and offered to write for her — in an interview six years later, Nellis said, “She is really, really talented. She wrote like she was a 35-year-old.”

As a high school junior in 2004, at Nellis' urging, Casey started a blog called Teen Fashionista — her first independent venture as a creator. Of course, nobody used the word yet; the closest analog was “blogger."

Fast-forward to today: Casey has been writing her youth trends newsletter After School for nearly three years. She says she started thinking of herself as a creator late last year, but even “a year ago, I was not comfortable with a creator title.” She still identifies as a writer and editor, first and foremost.

Even in 2016, when Casey and her friend Liza Darwin co-founded the newsletter company Clover Letter, they wouldn’t exactly have been considered “creators,” partially because the term wasn’t as broadly used yet, but also because they were more accurately “new media founders.” Regular readers of Creator Spotlight might argue: what’s the difference?

(Editor’s note: If you have thoughts on this, please let me know in a reply to this email!)

After School covers "Youth consumer trends + Gen Z insights." The concept forms a perfect circle with that column she wrote for fashion.about.com two decades ago, called "Casey's Clicks," with the tagline, "Stay on top of the latest teen fashion trends by checking out these articles, all written by teen fashion expert, Casey Lewis of teenfashionista.com."

Some things never change.

Two decades ago, blogs were the new newsletters; today, newsletters are the new blogs; and today, for the second time in her career, Casey is quitting her day job to work full-time on an independent newsletter project.

By one measure — the time from publishing the first issue of After School to today — it has taken Casey three years to build a 40,000-strong subscriber list for After School. By another measure — the time from her beginning to write about youth culture to now — it has taken 20 years.

One thing is crystal clear regarding Casey's career: she is endlessly fascinated by youth culture and how it shifts on both the day-to-day and generational levels. Whatever you can't stop thinking about, now is the time to start writing about it or creating videos about it, whatever your inclination.

Writing consistently about an obsessive interest on a timeline measured in years will make you a better writer and a relative expert on that topic. This is a foundational commonality between every successful creator: at one point, they just started doing their thing. And then they did it again. And again.

We recently spent an hour with Casey chatting about:

• 💵 Building and selling her first newsletter business (2016–2019)

• 📭 Writing her newsletter to 0 subscribers for the first month

• ✌️ Leaving a full-time job to commit to her newsletter business (again)

• 📈 Her premium subscriber model with a 5% conversion rate

• 👩‍🎨 Monetizing a curation-style newsletter

No time to read or listen to the rest? Before you go, here are a few quick lessons from Casey’s work on After School, applicable across niches and platforms.

1. Your first project won't always be "the one." After School is Casey's third proper foray into independent online publishing, and it's on track to be her most successful yet. Yes, this is partially due to experience; her teenage blog may have hit 20,000 pageviews some months, but it wasn't bringing in a six-figure yearly revenue. It's also due to timing — back in 2004, it wasn't as easy to monetize on Blogger as it is today on a platform like beehiiv (or even Substack).

2. Curation-style newsletters can be a highly valuable service but have to serve their creator first. At the core of it, After School rounds up need-to-know stories about youth trends five times a week. Casey was doing that consumptive research long before she started the newsletter; the newsletter turns her countless hours spent surfing the web (why did we stop using that term?) into a service for her readers. She’s harvesting the best bits and curating them.

3. Set ambitious goals; worst case, you still learn a ton. Casey and her co-founder Liza sold their newsletter Clover Letter for a decent but not life-changing sum. In the process, Casey’s eyes opened to the worlds of brand-building, marketing, email, and venture capital. For creators, career growth is as good a goal as monetization — it’s ultimately a step in that direction.

The following interview has been edited for length and clarity. You can listen to the full interview as a podcast on any major podcast platform. Just search for “The Creator Spotlight Podcast.”

You've been writing about teen culture since you were a teen. Teens then were Millennials, and now they're Gen Z. Will your coverage shift to Gen Alpha in a few years?

You're right that it's youth culture that I'm interested in, not Gen Z exclusively. When I was in college, I worked at this website called YPulse, which is a youth insights and intelligence company. It's changed a lot since, but at the time, it was a very scrappy website.

If you look it up, you'll see how that experience led me to doing After School — I was tasked with scouring the Internet for articles relevant to youth marketers.

I've been doing a version of this for a long time, but at that point, youth trends were about Millennials, and I was a Millennial. Throughout my career, I've reported on youth trends for both youth and adults. YPulse was for adults — people marketing to youth. Clover Letter was for teens. Now, with After School, I'm interested in telling teen stories for a combined audience of teens and adults.

You spent the first half of the 2010s working at Teen Vogue, then you left to launch Clover Letter. What’s the story there?

(🎙️ Editor’s note: Casey’s answer to this traces her and co-founder Liza Darwin’s three-year journey from leaving their jobs, starting Clover Letter, growing it, getting acquired by AwesomenessTV, and then leaving.

It’s all quite interesting, but too long for the newsletter. Curious? Listen to the podcast for the full story).

After Clover Letter you went to New York Magazine for two years before leaving and ultimately starting After School. Why did you decide to leave a full-time job again and start something new?

I love The Strategist, I love shopping content, and I wanted to learn about affiliate marketing. It was awesome, but it was also the pandemic, which made it a little bleak because we were doing pieces on, like, the best masks to wear. Also, after doing so much beyond editing with Clover Letter, I’d learned that just editing wasn't enough for me anymore, so I put in my notice and went freelance.

I have a high anxious energy and need something each day to look back on, to feel like I did something, or else I'm just unmoored. I've always been interested in youth trends, but with TikTok and everything else happening, it felt like I was consuming all of this stuff every day, and it went in one ear and out the other. I felt like there were some macro insights inside my brain, but they weren't living anywhere.

For the month of April 2021, I wrote After School every day without telling anybody. It was just an exercise: does this feel good for my brain? Is there enough youth consumer trend content to do this daily? What are the learnings?

I'd seen people say they were starting a newsletter but only end up sending out one issue, so I was afraid I was setting myself up for something untenable. Also, as a creator, the best work comes from doing something that you want to see exist. We've all read newsletters where you can tell this person is phoning it in because they decided on this cadence and now have to stick to it, but they don't know what to say or are clearly burnt out.

I wanted to make sure After School felt personally fulfilling and mentally feasible. And it was! So then, three years ago, in May, I went live and tweeted about it. It's been a slow and steady growth since then. I've learned a lot in three years.

What was it like writing to nobody for your first month? Did that exercise help you fully establish the bones of After School?

I felt protected sending the email to no one. I didn't have my byline listed. No one knew it existed; it was just for me. So why even publish it? But I did. Then I added my byline, and the fear was, what if I announce this thing, tweet about it, and no one cares?

When I started Teen Fashionista as a kid, I didn't tell anybody about it. I've always had a comfortable separation between my online and offline identities, and I don't talk to my family much about my online identity.

The format has changed a bit. I'm much more long-winded now — I'm obviously more comfortable in my opinions, but that's also from three years of researching this. I feel I have more to say. One thing that has been constantly evolving is the paid weekend edition.

I've started to make TikToks because it helps my subscriber growth. I also posted my first reel, which was terrifying because I have friends and family following me on Instagram. Putting myself out there in that way, I'm like, are they making fun of me in the group chats?

To a certain extent, you have to lean into the cringe, especially if you wanna grow online. If you're proud of what you're doing, what are you worried about?

Can we talk about your newsletter growth? You’re at 40,000 subscribers nearly three years after launch. Where have they come from?

Having grown Clover Letter and, to a lesser extent, having worked on Teen Vogue's newsletter strategy back in the day, I had a pretty good sense of what the numbers should look like in terms of open rate and sheer list size.

In 2015, Teen Vogue had a massive list but a terrible open rate, for the same reason we ran into with Clover — the dot-edu emails expiring. I’ve approached After School differently, especially because I wasn't trying to scale it. I was trying to do something for my own brain. I felt really strongly about that — if others benefited from it, great, but I was trying to find something that worked for me.

My growth was slow and steady, but my open rate was high. The beauty of an email newsletter is that, for the most part, you know who's signing up. I saw Nike, Instagram, Red Bull, and huge agency email addresses signing up, and it was such a thrill. Until a certain point, the growth was slow enough that I was literally looking up every person. I do not do that anymore, although I should. Knowing these people were reading it was encouraging, even though the growth wasn't lightning-fast.

I've never used any sort of growth tactic, like cross-promotion. That's probably a missed opportunity or something I'll pursue in the future, as so much of newsletter growth comes from cross-promotion.

Anytime someone tweets about me or gives me a shoutout in their newsletter, or when I've been in articles as a source recently, I might get a burst of followers, but not always.

You’re leaving your full-time job to build on the newsletter. Why is now the time?

I'm leaving with the team's blessing, but I've just been burning the candle at both ends. Producing the weekend edition takes my entire weekend. And look, we all work a lot, but working for a VC is not a nine-to-five.

Coming into the new year, After School saw a lot of growth, and I saw an opportunity here that I couldn't explore because I was already working full-time and didn't have the energy.

I'm planning to add a pro offering designed for brands, a monthly deep dive. That's when having the list of specific brand emails will come in handy. I can do some direct outreach, like, "Hey, I'm getting ready to launch this thing!"

What's After School’s monetization story? I know you have the premium offering and sometimes you sell ads.

I'd been doing it for a couple months, getting good feedback, and decided to try a premium plan. Substack was saying you could expect 10% of your subscribers to convert.

I turned on the premium option on July 18, 2021. At that point, I'd been doing the letter publicly for a couple of months, and I had 2,000 subscribers. The first time I sent an email promoting premium, 19 people signed up. That was not bad, but there were many weekends when I was putting so much work into the premium letter, and only 20 people were reading it. Then it grows, slow and steady, and you understand that those people believing in you, their buy-in is enough to make it worth your time.

I spend so much time diving into weird rabbit holes on my weekend already. Writing the newsletter, I come out of it having learned so much, and that's worth it especially because it's paid now. I feel such an intellectual payoff learning about all these brands and things people are doing on TikTok.

To be totally candid, I'm at 40,000 subscribers and I've consistently had about 5% convert. So, we're looking at a good amount of premium subscribers. It's never risen past 5%, but it's been steady; that equates to a good amount of money now.

I've explored partnerships and ads. I'm interested in beehiiv's tools around that because I don't have the bandwidth myself to activate that channel. In the last year, doing my full-time job as well, I've had brands reach out and I honestly leave them on read because I'm like, I can't.

Has anything you’ve done driven spikes in premium signups?

Anytime I do a TikTok haul deep dive, like the Christmas list haul and the back-to-school haul, those always convert big-time, but they’re unfortunately not easily replicable. It's not like I can do that every week.

I was also lucky enough to be on CNBC live TV talking about the public markets segment, which finance guys watchThat was really funny because I know nothing about finance, and they wanted to talk about Stanleys and the implications of that on the public market. Immediately after, I had a lot of new subscribers, paid and otherwise. I think the people working on private or public market stuff have big budgets and need to know consumer shifts. I had a lot of analysts connecting with me on LinkedIn, which has never happened before.

Are you able to support yourself with premium subscription revenue? How are your financials?

I could definitely support myself. I’ve had a full-time job this year, so that’s been nice, but it’s also been very hard mentally to do both. Add a little bit of ad revenue and partnerships, and I could support myself.

Something I’ve looked to as inspiration for this pro offering I’m gonna try is Ryan Broderick’s Garbage Day. He does an interesting monthly recap and data dive. That got me thinking — if you think about my dailies as micro trends, there’s some interesting macro stuff to look back on, like what the hell happened this month? I’m gonna try it.

How to monetize a curation newsletter

(Editor's note: Longer analysis in this section today. Let me know if you appreciate it using the poll at the bottom of the newsletter.)

After School is a curation newsletter, a content genre that involves aggregating links to original content other people have produced and published online, within a defined niche.

After School rounds up content about youth culture trends, sometimes including content that might not be relevant to the topic on the surface but that Casey shows to be relevant. The 4x weekly free editions usually include 11 links alongside very light commentary. I checked out one of the weekly premium editions: 74 links to other stories. Assuming no overlap, that's at least 118 stories, articles, and videos Casey consumes in a week — not to mention other content not relevant to her work.

Ok. On the surface, a curation newsletter is easy to produce because you're just finding and compiling a bunch of semi-related links. Anyone who spends an hour every morning reading content and browsing news sites can do this, right? No.

After School has an audience of 40,000 with an approximate 5% conversion rate to premium subscriptions — there are currently about 2,000 premium subscribers.

Assuming all those premium subscribers are on the cheapest possible plan, including Substack's 10% take on premium subscriptions, and not including any ad sales or taking out taxes, we can estimate that After School is currently generating a revenue of around $130,000 per year. By the way, that is $24,000 more per year than the highest listed salary for any editorial position on Conde Nast's job listings at the time of writing — the company that owns both Teen Vogue and New York Magazine, where Casey once worked.

The service Casey provides to premium subscribers is her obsessive interest and expert knowledge of youth culture trends, combined with her understanding of, ability to navigate, and processing of the digital media landscape. She spends hundreds, maybe thousands of dollars on content subscriptions each year (a 50-50 mix of traditional outlets and creators, she says) — and a great deal of time processing all that content. She couldn't quantify it when asked; that process is inseparable from her day-to-day and has been for years.

Especially in After School's premium-only, long-form weekend edition, Casey makes connections other people don't see between stories and content they wouldn't otherwise find. Think of the premium subscription as a one-to-many consultancy.

This is how you monetize a curation-style newsletter:

• Be authentically interested in a topic.

• Build a high-input consumption habit around it.

• Give away most of the links for free.

• Provide in-depth analysis behind a paywall.

Content we've been thinking about while working on this issue.

• I discovered Brad Esposito’s Very Fine Day newsletter during research for this issue (he interviewed Casey two years ago). His recent issue “The only way media will get better” places faith in small, high-quality publications as the enduring next chapter of media.

• beehiiv is working with Carry on an eight-day virtual summit, “The Business of One (For Solopreneurs). Each day has a different theme — something in there for all kinds of creators and entrepreneurs. Register here.

• Spotlight reader, philosopher, and podcast consultant Tanner Campbell was inspired to write an article on our attempt to define “creator” in last week’s issue. A good, quick read!

Thank you for taking the time to read today's issue. If you liked this one, I highly recommend listening to the podcast version. We already have at one five-star review on Spotify!

On to next week's issue, featuring a creator who has been in the game for two decades. He’s a musician who helped pioneer what it means to create on YouTube and has, in recent years, focused his energy largely on educating other musicians and creators through his content. He also published a book on being a creator last month — send me a reply if you think you know who it is!

— Francis Zierer, Editor