Ryan Broderick is the creator of Garbage Day, “A newsletter about having fun online.” He’s among the most popular journalists-turned-newsletter-creators out there. It’s clear by the numbers (68k subscribers, 3k of whom pay for premium content), praise from other creators, and the nearly 200 press clippings on his About page.

In this episode we discuss:

• 📰 There’s (almost) no difference between journalists and creators
• 🛋️ Why you need a Simpsons couch gag in your newsletter
• 🫵 Every American is a journalist (if they want to be)
• 🚖 Creators are Uber drivers for content
• 🧑‍🎓 Garbage Day is on the syllabus

Intro music produced by J. & Doug Organ.

Jared Dashevsky runs Healthcare Huddle, a twice-weekly newsletter for physicians and other healthcare professionals. In just over four years, he’s built an audience of 30,000. He’s also built a team of 13, dismantled that team and been acquired. But today, Jared is once again a solo creator.

In this episode, we discuss:

• 🎓️ The cap on how far Healthcare Huddle can or should scale
• 😍 Understanding your newsletter’s “true fans”
• ✍️ Creating a sustainable newsletter workflow
• 🧠 Jared’s four key lessons from four years of newslettering
• ↩️ Pivoting from a B2C to B2B audience

Intro music produced by J. & Doug Organ.

Arielle Nissenblatt knows podcasts. She writes a weekly newsletter about podcasts, hosts a podcast version of that newsletter, co-hosts another weekly podcast and a daily podcast. She runs a Discord community for podcasters. On top of all that, she works full-time as a community marketing manager at Descript.

In this episode, we discuss:

• 🤝 How Arielle broke into the podcasting industry
• 🎙️ Why you should not start a podcast (unless you should)
• 🫂 What “community” means to brands and creators
• 💖 The potential of creator advocacy organizations
• 🏠 How brands should work with in-house creators

Intro music produced by J. & Doug Organ.

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

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