The Creator Spotlight Podcast Creator Spotlight

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 from a career in PR to indie creator work🤳 Building a newsletter audience by building a TikTok audience
00:00 What is The Deep Dive
02:30 Being a curator
06:23 What is a video essay?
14:26 Going viral on TikTok
19:04 Why start a newsletter?
24:21 Why we need curators and gate-creators
28:22 The stats - How to grow subscribers
33:32 Haya’s premium newsletter, The Rabbit Hole
37:27 Monetisation and referrals
41:47 Advice for creators and lessons learned

Intro music produced by J. & Doug Organ.

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🤝 Working in community with other creators
00:00 Who is PJ Milani
01:25 Why PJ started creating — Getting on social media
09:04 How to gain 200k followers
14:48 Relationship between writing and drawing
19:39 Which social media platform is best — Twitter vs Instagram vs LinkedIn
23:57 How to convert social media followers into newsletter subs?
30:56 How PJ monetises his content
42:23 The long term plan

Intro music produced by J. & Doug Organ.

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 syllabusIntro 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 audienceIntro 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 creatorsIntro 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