How to Grow and Monetize a Newsletter in 2027 (Full Strategy) | Chenell Basilio | 153

As the founder of an email marketing platform, you’d think my newsletter would be dialed in. But it turns out there's a lot I could be doing better. I think that's true for most creators, who get so caught up in growth hacks that their list slowly dies out or hits a plateau they can't get past. Chenell Basilio reverse engineers how the biggest newsletters grow and took her own newsletter, Growth in Reverse, to 21,000 subscribers in just 10 months. In this episode, Chenell walks me through the 5 levers behind newsletter growth, including how to make your content insanely valuable, how to build momentum with tactics like quizzes, and the one lever she sees hardly anyone using. Then she applies all of it to my own newsletter, from the headline on my site to how I share podcast episodes, and it turns out I have some work to do. If you're trying to grow your newsletter and want a total masterclass in how to do it, this is the episode for you. Timestamps: 00:00 Introduction 01:37 Why growth tactics are only 1 of 5 levers 02:03 How Chenell hit 21,000 subscribers in 10 months 03:29 Why going deeper than everyone else stands out 04:40 Lever 1: Insanely valuable content 06:24 6 ways to make content insanely valuable 08:34 Mario Gabriele's S-1 breakdowns 10:11 Making readers the smartest person in the room 12:40 Why you should get on calls with your readers 13:28 Lever 2: Positioning 13:55 How a food waste app became The ADHD Weasel 16:05 Why positioning changes over time 18:54 How to find readers to talk to 20:28 How reader calls shaped Sam Vander Wielen's bundle 21:19 Lever 3: Building momentum 21:56 Why you should pick one platform 22:15 Why quizzes are working so well 26:21 The quiz that 9X'd The ADHD Weasel's growth 27:16 How to get noticed by creators you admire 28:46 Building a quiz for The Ladders of Wealth 29:47 Lead magnets that don't need new content 30:39 Using AI skills as lead magnets 32:01 Why you should post more on social 35:05 How to mine your best content 38:34 Why it's okay to repeat your best stories 39:43 Lever 4: Conversion 41:55 Chenell's spicy take on Linktree 43:35 How Dru Riley got a landing page to 40% 45:55 Why the wrong views won't convert 48:27 How Pat Walls positioned Starter Story's paid product 50:54 Lever 5: The one hardly anyone is doing 51:39 Why you need an "almost there" page 53:24 What makes a great welcome email 55:52 How to surprise new subscribers 58:21 Doing what bigger creators can't 1:02:12 Why you should subscribe to your own newsletter 1:03:55 Chenell audits Nathan's newsletter 1:06:38 The bar for Nathan's newsletter content 1:09:20 Splitting the podcast into its own email 1:11:36 Turning the book launch into content 1:13:44 Chenell reads Nathan's homepage headline 1:16:36 Sharing your success without bragging 1:18:42 Promoting the newsletter inside episodes 1:22:56 Fixing Nathan's conversion points 1:26:14 The hidden cost of double opt-in 1:29:49 How newsletters monetize 1:31:46 Why Packy McCormick's sponsored deep dives work 1:33:19 Group coaching and high-ticket offers 1:36:00 The pricing sweet spot for memberships 1:37:26 When paid newsletters work 1:40:48 How to price a paid newsletter 1:43:57 Final thoughts If you enjoyed this episode, please like and subscribe, share it with your friends, and leave a review. I read every single one. Learn more about the podcast: https://nathanbarry.com/show Follow Nathan: Instagram: https://www.instagram.com/nathanbarry LinkedIn: https://www.linkedin.com/in/nathanbarry X: https://twitter.com/nathanbarry YouTube: https://www.youtube.com/@thenathanbarryshow Website: https://nathanbarry.com Kit: https://kit.com Follow Chenell: Instagram: https://www.instagram.com/chenellco X: https://x.com/chenellco LinkedIn: https://www.linkedin.com/in/chenellco YouTube: https://www.youtube.com/@growthinreverse Website: https://growthinreverse.com Featured in this episode: Kit: https://www.kit.com Growth In Reverse: https://growthinreverse.com Newsletter scorecard: https://growthinreverse.com/scorecard The Generalist: https://www.generalist.com The ADHD Weasel: https://adhdweasel.substack.com Trends.vc: https://trends.vc Starter Story: https://www.starterstory.com The Ladders of Wealth: https://laddersofwealth.com Highlights: 06:24 The 6 ways to make content insanely valuable 26:37 The quiz that 9X'd The ADHD Weasel's daily growth 50:54 The growth lever almost no one is using 1:13:44 Chenell roasts Nathan's newsletter 1:31:46 How Packy McCormick gets paid 5 to 10X for sponsored deep dives