Kate Lindsay is a freelance writer and newsletter editor whose own newsletter, Embedded, is pushing 35k subscribers. She's one of the best people out there writing about the internet for the internet. This is an episode about why more newsletters should be run by two people, an indie newsletter born from a shuttered publication, and paying NYC rent with premium newsletter subscriptions.00:00 Who is Kate and what is Embedded?05:33 How Embedded evolved from a killed publication09:56 Kate's other projects (as a newsletter editor and writer)13:35 Blowing up with the Millennial Pause16:44 Being an editor vs. a writer19:09 What is a newsletter? What is a creator?27:42 The stats — how to grow a newsletter34:22 Are creators the new journalists?38:49 Advice for online creatorsIntro music produced by J. & Doug Organ.

Today’s guest, Andrew Southworth, always wanted to become a musician. To do so, he became a mechanical engineer. Last year he quit his day job to make music and help other people market their music full time. He does YouTube, newsletters, courses, he has an agency — he does it all. We spoke about:📆 A 13-year long bet to become a creator-entrepreneur🪴 How to diversify, effectively, as a creator🤔 Can you over-diversify?00:00 Andrew Southworth's many businesses04:27 When to hire as a creator07:47 How Andrew makes money09:42 16 years of being a YouTuber19:33 Why Andrew started a newsletter22:47 Andrew's future plans and dreams25:10 Advice for other creators

Today’s guest is Akhil Chauhan, who runs The Writer’s Job Newsletter (TWJN). But he didn’t create the newsletter — he acquired it.Akhil has been running TWJN solo (besides occasional social media help) for two years. The guy he bought it from ran it for only one year. We spoke about:💰️ The economics of a newsletter acquisition🤐 Keeping his personality (mostly) out of the newsletter🤝 Pulling off a seamless handoff after acquiring the newsletter🧑‍💼 Being accountable to subscribers who rely on the newsletter for jobs00:00 Acquiring a newsletter 08:05 Researching solo 14:10 The differences in journalism in the UK vs US 15:35 Growing a newsletter to 10k+ subscribers 23:18 Work/life balance as a creator 29:23 Premium subscribers and monetisation 33:04 Keeping a distance from your audience 36:50 Advice to creators, from a creator 41:05 The future of TWJN 45:30 The biggest regret as a creator Intro music produced by J. & Doug Organ.

Peter Ramsey of Built for Mars shares his journey from accidental consultancy to viral bank study. Topics include newsletter monetization, UX gamification, and content creation challenges. He discusses the diverse audience of Built for Mars, the future of online businesses, and his disdain for social media.

Today’s guest is Caitlin Murray, better known by her Instagram handle @bigtimeadulting. After her son was diagnosed with leukemia in 2016, she started writing about it to friends and family — nearly 8 years later, she has 1.4 million Instagram followers. It’s a great story.In today’s episode:00:00 The origin story05:50 How to gain over 1 million followers10:15 The 4 chapters of @bigtimeadulting14:15 Turning Instagram into a business19:25 Building a positive community24:08 Growing an Instagram following, organically29:22 Podcasting is hard33:41 Monetizing as a creator38:31 Starting and building a newsletter47:45 Having multiple monetization streams51:53 Advice lightning roundIntro music produced by J. & Doug Organ.

Today's guest is Tyler O’Shea, creator of Joker Mag, a website and newsletter about sports underdogs. He started the project in that “what am I gonna do with my life” period after graduating college. Nearly 7 years of posting later, he’s still doing it as a side project, but it’s also led him to a career in SEO (search engine optimization).In this episode, we talk about:🐶 Learning how to write for the internet🌟 What writing and posting content online can do for you🔎 How posting led Tyler to discover and start working in SEO📱 How to figure out which social media platform is most useful for youNote: Yes, Francis' sound is slightly off in this episode. Good thing Tyler does most of the talking!00:00 Tyler’s motivation and the mentality of a creator 05:37 The inspiration to start writing 08:40 Is Google’s AI killing SEO ?11:36 The average Joker Mag reader 14:44 Finding amazing sports stories 18:37 How to grow a loyal audience 23:25 How much time does it take to grow a newsletter? 27:38 The different monetization channels 32:03 Hiring other writers 37:21 SEO tips: How to make your website the best 39:06 Advice for creators 43:40 Future goals 49:30 Quick Q&A Intro music produced by J. & Doug Organ.

Today's guest is Kate Samuelson, co-creator of Cheapskate London. Every Monday, they send out a newsletter built around free events, two for each day of the coming week. Over the last five years they’ve built an audience of over 19k, winning praise from longstanding media institutions in the process.All the while, Cheapskate is a side project; during the day, Kate works as a journalist. She specializes in newsletters.In this issue:🍸️ Giving subscribers a free bottle of gin as a referral reward📰 Operating a newsletter while working full-time in journalism💷 Running paid ads for your newsletter is easier than it sounds00:00 What is Cheapskate London? 06:10 Who is the average reader? 10:03 Choosing what content to include — curation17:36 Kate’s career as a journalist30:45 The stats — how to grow an audience38:42 Kate’s unique referral program — giveaways!41:58 Monetization 52:49 Advice for newsletter creators Intro music produced by J. & Doug Organ.

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 audience00:00 What is The Deep Dive02:30 Being a curator06:23 What is a video essay?14:26 Going viral on TikTok19:04 Why start a newsletter?24:21 Why we need curators and gate-creators28:22 The stats - How to grow subscribers33:32 Haya’s premium newsletter, The Rabbit Hole37:27 Monetisation and referrals41:47 Advice for creators and lessons learnedIntro 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 creators00:00 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.