'LetterLand

This week on Letterland LIVE we're joined by Taylor Craig, founder and CEO of Launch Live Now. Taylor helps media brands and creators launch live shows. We'll dig into why live is a massive blue ocean opportunity for newsletter operators, what actually makes a live show work, and how to find winning content formats. We'll also get into: 🤖 Sponsors are quietly blacklisting AI-heavy newsletters 📺...

This week on Letterland LIVE, we welcome 1440 founder and CEO Tim Huelskamp. Tim built 1440 into one of the biggest daily newsletters in the world. We'll get into the playbook behind scaling a daily news digest to millions of readers, the economics of the aggregation model, and where he sees opportunity in the newsletter space heading into the second half of 2026. We'll also get into: 📱 A new pla...

This week on Letterland LIVE we're joined by Growletter founder Matt McGarry and newsletter sponsorship strategist Heather Hunter. We're talking about the new kings of media, a huge AI opportunity for newsletters, and how to find love in the inbox. Plus everything else you need to know about the newsletter world. Subscribe to never miss a Letterland LIVE: https://www.youtube.com/@LetterlandLIVE Jo...

This week on Letterland LIVE we're joined by MarketBeat founder and CEO Matt Paulson and DNNR co-founder Rae Lambert. Matt is a legend of the finpub space who's grown MarketBeat to $60M+ in revenue. We'll get into how to keep your media business lean, whether starting a newsletter in 2026 is even worth it, and how many emails you should be sending subscribers. Rae founded DNNR in 2023 to help crea...

A newsletter just hit a $101M valuation, without raising a dime. We break down 1440's jaw-dropping numbers and what it means for the business of newsletters. We also discuss... 💰 The Rundown's first strategic investment 📬 The Flyover's $5M crowdfund 🐝 Inside beehiiv's rise to $30M ARR with employee #7 Daniel Berk 🔍 AEO strategist Kaleigh Moore breaks down AI search 📧 Our daily newsletter goes...

Do BuzzFeed, Business Insider, and other pageview/scale era media companies still have some life left in them? We chat with Industry Dive founder Sean Griffey about what everyone is missing in the pageview media model. We also discuss... 🍾 Workweek's Partner Platform launch with Adam Ryan 🔮 Substack's Once and Future Media Forum 🐝 Beehiiv's Summer Release Event ⛰️ Starter Story's starter story...

In this special holiday edition of LetterLand, Louis and Tyler look past 2025 to predict the massive shifts coming to the newsletter and creator economy in 2026. From the death of the "middle class" newsletter to the surprising B2B sales strategies borrowed from OnlyFans, they break down why the old playbooks are breaking and what will replace them. Follow Louis: https://x.com/louisnicholls_ Follo...

In this episode, Louis and Tyler sit down with Ryan Sager, co-founder of Who Sponsors Stuff , to break down how to monetize your newsletter through live events. We explain why you should stop chasing celebrity speakers and how to get sponsors to cover your costs before you spend a dime. Ryan also shares how a small dinner series evolved into a successful conference and the best way to validate you...

This week, Louis and Tyler examine how to convert social media followers directly into newsletter subscribers using DM automation, effectively bypassing the friction of traditional landing pages. They break down the mechanics of "borrowing" audiences from other creators, outline strategies for securing free recommendations through strategic interviews, and share tactical advice on using tools like...

In this episode, Louis and Tyler sit down with Matt Paulson, founder of MarketBeat, to break down what it takes to build a $50M media company. We talk about why obsessing over cost per subscriber is killing your growth and reveal the exact metrics to focus on instead. Matt also shares how to generate $1.5M a month with SMS marketing and why niching down is actually bad advice for building a massiv...

In this episode, Louis and Tyler sit down with Nathan May, founder of The Feed Media, to break down the "Invite-Only" newsletter blueprint. We explain why selling ads is a trap for most creators and reveal the exact math on how to generate $1M in revenue with just 1,000 subscribers using a high-ticket, exclusive model. Follow Louis: https://x.com/louisnicholls_ Follow Tyler: https://x.com/JPMorinC...

This week, Louis and Tyler break down the escalating newsletter platform wars. Patreon launches Quips to clone Substack Notes and pull creators back, Beehiiv drops a massive feature batch in full catch-up mode, and the fight for creator loyalty intensifies. They analyze why Patreon suddenly feels dangerous, where Beehiiv is vulnerable, and what this means for operators choosing platforms. Follow L...

In this episode, Louis and Tyler sit down with Matt McGarry to break down 5 7-figure newsletter ideas you should steal and launch this weekend to hit a million dollars in revenue in 2026. Matt's stuff (go follow him): https://growletter.com Follow Louis: https://x.com/louisnicholls_ Follow Tyler: https://x.com/JPMorinChase Subscribe for more!

How did a college kid with no network or experience manage to break into venture capital... one of THE toughest, most cliquey industries in the world? Brett Perlmutter of BulletPitch joined Louis and Tyler on the pod to share all 👇 → how he came up with the idea for his newsletter → crazy growth hacks that drove thousands of high quality subscribers → and how things ended up going so well he real...

This week, Louis and Tyler dig into the top 5 ways to get your first 1000 subscribers that actually work to build a profitable newsletter business quickly.

This week, Louis and Tyler examine whether Substack is siphoning readers from your owned channels, how its network effects impact discovery and retention, and how to keep control of your list. They compare native recommendations vs external links, outline migration and backup steps, and share metrics to track platform risk.

In this episode, Louis and Tyler are joined by Corey Leff, Founder and CEO of JohnWallStreet.com , to show how a niche B2B newsletter became a sports intelligence business. They cover writing for 100 who matter, mentor-driven access, brick-by-brick growth, sponsor-led events, $10k memberships, thematic research, and why free beats paywalls. Follow Louis: https://x.com/louisnicholls_ Follow Tyler:...

In this episode, Louis and Tyler are joined by Ryan Heafy from 6AM City to share the playbook for scaling local newsletters. They cover market selection, AI-assisted workflows, internal tools, list growth, ad sales, and the deliverability habits that keep engagement high. Follow Louis: https://x.com/louisnicholls_ Follow Tyler: https://x.com/JPMorinChase Subscribe for more!

This week, Louis and Tyler unpack a wild cash-drop stunt to grow a newsletter. What worked, what flopped, and the exact fixes to turn fleeting views into email subscribers. You’ll learn how to sharpen the CTA, tighten the landing page, and craft an offer people actually want so a viral moment becomes a list-growth engine. Follow Louis: https://x.com/louisnicholls_ Follow Tyler: https://x.com/JPMor...

In this Q&A episode, Louis and Tyler are joined again by Emanuel (Manu) Cinca from Stacked Marketer to answer listener questions. They discuss how to pitch starting a newsletter at an established brand, the most impactful ways they're using AI to improve their newsletters, and the unexpected challenges that will be much harder than you think when starting out. Follow Louis: https://x.com/louis...

In this episode, Louis and Tyler are joined by Emanuel (Manu) Cinca from Stacked Marketer to discuss how to start, grow, and monetize a B2B newsletter in today's competitive landscape. Follow Louis: https://x.com/louisnicholls_ Follow Tyler: https://x.com/JPMorinChase Subscribe for more!

In this episode, Louis and Tyler are joined by Jeffrey Eisenberg from Media Intercept to discuss newsletter advertising, monetization strategies, the future of ad networks and hot takes on the newsletter space in 2025. Follow Louis: https://x.com/louisnicholls_ Follow Tyler: https://x.com/JPMorinChase Subscribe for more!

In this Q&A episode, Tyler and Louis dive into strategies for landing your first newsletter sponsorship, including tips on leveraging your subscriber list, analyzing competitors, and using ad networks. Plus a bunch more newsletter questions and answers... Follow Louis: https://x.com/louisnicholls_ Follow Tyler: https://x.com/JPMorinChase

It's 2025... a whitepaper or cheatsheat won't cut it anymore if you want lots of newsletter signups. So how do you create lead magnets that actually work? Tyler and Louis discuss our top 5 lead magnets to try this year for faster newsletter growth. Plus — are newsletter open and click-through rates dead? Or still useful?

Substack raises a $100m series C round of funding from top investors. What does this mean for the newsletter space? Should we all move to Substack now? Will they finally embrace ads?  Join Louis and Tyler for our first ever (excuse for an) "emergency pod", as we give our first impressions and hot takes on the news.