Today's guest is Haya Kaylani, creator of a curation-style newsletter called The Deep Dive. What does she curate? YouTube video essays, five of them every Wednesday. She’s built an audience of 92k TikTok followers and 13.5k newsletter subscribers in just 15 months — pure organic growth, with almost all of her newsletter subscribers coming over from TikTok. In this issue, we discuss: 🎨 Curating, gatekeeping, and gatecreating📺️ Why writing about YouTube is a huge opportunity📢 Applying lessons...

Today's guest is PJ Milani, a high school animation teacher recently turned social media star. He’s known for his “visual metaphors” — single-panel illustrations featuring lessons about life and creativity. Across his socials he has over 200k followers, his newsletter has 16k subscribers, and he teaches a perennially sold-out cohort course about visual thinking on Maven. In this issue, we discuss: 🌱 Organic growth🔜 Trusting the process, every day🎨 What it means to live a creative life🤝...

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...

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...

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...

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...

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...

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...

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...

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💰...

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...