'LetterLand

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_Follow Tyler: https://x.com/JPMorinChaseSubscribe for more!

Ryan Sager, co-founder of Who Sponsors Stuff, brings his extensive media experience to discuss monetizing newsletters through live events. He reveals how he transitioned from editorial roles to leveraging newsletters for revenue. Ryan shares the success story of transforming intimate dinner gatherings into profitable conferences, emphasizing the importance of local sponsorship models over ticket sales. He highlights effective ways to validate event ideas and stresses the value of choosing operational speakers over celebrities for greater impact.

Discover innovative strategies to turn social media followers into newsletter subscribers using automated DMs. Learn how to effectively borrow audiences from other creators and secure free recommendations. The hosts share insights on using ManyChat for organic growth and emphasize collecting emails through direct chats. They discuss the power of lead magnets and reciprocal strategies for subscriber exchanges. Plus, find out how hosting paid events can boost your reach while collaborating with fellow creators!

Matt Paulson, founder and CEO of MarketBeat, shares insights on building a multi-million dollar media empire. He emphasizes that focusing too much on subscriber costs can hinder growth. Instead, he advocates assessing ROI and tracking revenue at the subscriber level. Matt reveals how SMS marketing can generate significant revenue and warns against chasing vanity metrics that could harm deliverability. He also presents a contrarian view, suggesting pursuing larger markets over niching down. Tune in for fascinating strategies to supercharge your newsletter growth!

Nathan May, founder of The Feed Media, discusses his journey in building a successful invite-only newsletter. He shares why relying on ads can be a pitfall for creators and explains how to generate $1M in revenue with just 1,000 subscribers through high-ticket models. Nathan reveals strategies for using social proof and scarcity to boost demand, and stresses the importance of founder-authored content for building trust. He also identifies the best niches for invite-only newsletters and provides tips on scaling without losing exclusivity.

Louis and Tyler dive into the fierce newsletter platform wars, highlighting Patreon's launch of Quips to challenge Substack. They debate whether this will enhance creator discoverability or create a paywall experience. Beehiiv's new features spark discussion about their all-in-one approach and the risk of shallow integrations. Meanwhile, they imagine building newsletters with $100k, sharing unique, niche ideas. Finally, they introduce Sparkloop’s welcome offers to improve monetization and reshape advertiser relationships in the newsletter space.

Matt McGarry, founder of Growletter and former creator of Newsletter Operator, shares innovative strategies for building lucrative newsletters. He presents five million-dollar newsletter ideas, including dyslexia-focused content and B2B case studies. Matt discusses monetization methods ranging from memberships to courses, and the potential of AI-driven newsletters. He highlights the importance of personal branding and offers growth tactics using LinkedIn video and engaging founder group chats for insights. Ideal for aspiring newsletter creators!

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 realized he didn't even WANT a job in VC anymore... he could start his own damn fund

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.