Ryan Sneddon runs Naptown Scoop, a local newsletter serving Annapolis, Maryland. In three-and-a-half years, he’s built an audience of over 18,000 (nearly half the town’s population), and last year the business generated around $200,000 in revenue.

In this episode, we discuss:

• 🏘️ How Ryan got half the town to sign up for the Scoop
• 👩 Exactly how Ryan defined his core reader
• 💲 How Ryan prices the newsletter’s ad spots
• 👀 The Scoop’s simple and incredibly effective referral system
• 📈 Ryan’s plans to increase revenue by 175% this year

Ali built an audience of over 7,000 subscribers before he even sent the first issue of his newsletter, AI for Work. He would only end up sending 13 issues before (at approximately 30,000 subscribers) he went looking for advice on how to monetize and ending up selling the whole thing instead.

We spent an hour discussing:

• 🧲 How he built an ingenious, highly successful lead magnet
• 👀 Emailing every new subscriber to build relationships
• 💰️ Experimenting with monetization
• 🤖 Using TikTok to grow his email list (without making his own videos)
• 📰 His plans to start a local news newsletter

Intro music produced by J. & Doug Organ.

Andrew Huang is lifelong musician and a pioneer in the Creator Economy. He made his first dollar online auctioning off songwriting commissions on eBay two decades ago and has since became a celebrated YouTuber with 2.36 million followers, produced commercial commissions for international brands, and published a book.

Make Your Own Rules: Stories and Hard-Earned Advice from a Creator in the Digital Age came out in February 2024. We spoke with Andrew shortly after about:

• 📍 Why he focuses his output on just a few platforms
• 🧑‍🏫 His approach to creating his online music production course
• 🪞 Scaling as a creator without losing authenticity
• 📕 Writing this book (his first) and giving timeless advice

Casey has been writing the youth consumer trends newsletter After School for three years, the culmination of nearly two decades writing and editing content about and for teens in her own online publications and in Teen Vogue and New York Magazine.

On the occasion of Casey leaving her day job to work full time on a newsletter — for the second time in her career — we spoke 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

Read our feature on Casey and subscribe to our newsletter for more behind-the-scenes stories from the creator economy.

Eric, alongside Slava Rubin (host of the Smart Humans podcast), co-founded Vincent in 2019 as an aggregator platform for alternative investment opportunities. It's evolved into a media company with three newsletters and a podcast, still focused on alternative investments. Adam joined the team a couple of years ago as a researcher and writer.

We spoke about:

• 🏋️ Building a solid core audience over four years
• 📰 Deciding not to put names on the newsletter byline
• 👎 Knowing what not to write about
• 💰 Generating revenue through partnerships and trust
• 😌 Not worrying too much about competitors

Hannah started the TikTok page Salary Transparent Street two years ago. It now has 1.3 million followers — 2.8 million across all channels — and is a full-fledged media business, with $1 million revenue just last year.

Read our feature on Hannah and subscribe to our newsletter for more behind-the-scenes stories from the creator economy.

We spoke with Hannah about:

• 🫂 Building a brand based on audience trust
• 💵 The “Three C’s” at the core of her pay transparency mission
• 🎤 The art of the street interview
• 📈 Turning viral content into a sustainable business
• 🤝 Navigating brand deals with integrity