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Louis Nicholls and Tyler Morin dissect what the f happened in the newsletter space this week. Sometimes with "famous" guests.

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Artwork for 'LetterLand

Latest Episodes

This week on Letterland LIVE we're joined by Simon Owens, founder of Simon Owens' Media Newsletter.

Simon's been tracking the media and newsletter space for years, and we're getting his read on the two biggest stories in the industry right now: Subs... more

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Is the newsletter industry's favorite metric officially dead? This week on Letterland Live, Tyler Morin and Louis Nicholls break down the news out of France that could spell the end of email open rates as we know them — and what it means for how you ... more

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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 actua... more

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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 ... more

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Recent Guests

Taylor Craig
Live show operator and founder of Launch Live Now
Launch Live Now
Episode: Smart Newsletter Operators Are Going Live in 2026
Tim from 1440
Editor/leader at 1440 Explorers, discussed expansion beyond newsletters
1440
Episode: The Contrarian Approach to a $100M Newsletter
Heather Hunter
Newsletter sponsorship strategist
Independent
Episode: The New Kings of Media – with Matt McGarry and Heather Hunter
Matt Paulson
From MarketBeat (FinPub space)
MarketBeat
Episode: Substack breaks into the ad game, MarketBeat's Matt Paulson & DNNR founder Rae Lambert
Rae Lambert
Founder of Dinner (DNNR)
Dinner (DNNR)
Episode: Substack breaks into the ad game, MarketBeat's Matt Paulson & DNNR founder Rae Lambert
Dan Berk
Former Beehive employee; host of Moneywise podcast
Beehive / Hampton
Episode: Can you build a $100M newsletter without investors?
Kaleigh Moore
AI/SEO expert
Context Window
Episode: Can you build a $100M newsletter without investors?
Adam Ryan
Recurring guest on LetterLand, founder/leader at Workweek?
Workweek
Episode: Is everyone wrong about BuzzFeed?
Sean Griffey
Founder and former CEO of Industry Dive; media veteran
Industry Dive
Episode: Is everyone wrong about BuzzFeed?

Hosts

Tyler Morin
Host of LetterLand
Louis Nicholls
Host of LetterLand

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Talking Points

Recent interactions between the hosts and their guests.

What's next for newsletter sponsorships? With Jeffrey Eisenberg
Q: Do inline placements or dedicated sends perform better?
Dedicated sends are preferred by advertisers for guaranteed share of voice and highly qualified clicks, but publishers should limit frequency and ensure brand alignment to avoid subscriber churn; inline placements can work when crafted to fit the newsletter format and audience.
Q&A: How to sell your first newsletter ad (and more questions)
Q: Are there any good AI written newsletters?
There are likely high-quality AI-assisted newsletters that aren't obviously AI-written yet. The trend suggests that someday a major publication may be largely AI-generated, but successful newsletters will still rely on human oversight, unique voice, and expert-level editing to remain credible and engaging.
Q&A: How to sell your first newsletter ad (and more questions)
Q: Do cross-promos still work for newsletter growth, or is everything just recommendation widgets now?
Cross-promos can work, especially in the early stages, but they don't scale well as you grow. A balanced approach that leverages easy-to-scale recommendation widgets and selective cross-promotions, possibly aided by a VA, can yield steady growth without overloading your workflow.
Q&A: How to sell your first newsletter ad (and more questions)
Q: How can I find my first sponsors?
Start by surveying your existing list for potential business-aligned buyers, then consider inbound outreach to those brands, using tools to identify fitting advertisers and reach out with a clear media deck and case studies; testing with a small inbound campaign or a pilot ad can help you prove the concept before broader outreach.
The New Kings of Media – with Matt McGarry and Heather Hunter
Q: What are the most promising revenue channels for newsletter operators right now?
A mix of services (done-for-you offerings), events, and cohort-based courses, alongside continuing to invest in long-form, editorial sponsorships described as narrative capital rather than traditional ads.

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Frequently Asked Questions About 'LetterLand

What is 'LetterLand about and what kind of topics does it cover?

This show analyzes recent shifts in the newsletter ecosystem, with a steady emphasis on monetization, growth tactics, and platform dynamics. Episodes frequently feature operator-focused guests and veteran media founders who share practical playbooks for building sustainable newsletter businesses, including strategies around audience growth, monetization, events, and first-party data. A standout pattern is the hands-on approach: guests often discuss real-world campaigns, distribution levers, and partnerships, along with critical takes on dominant platforms and evolving sponsorship models. The format tends to blend contrarian perspectives with tactical advice, making it valuable for operators, marketers, and investors exploring newsletter-bas... more

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Which podcasts are similar to 'LetterLand?

These podcasts share a similar audience with 'LetterLand:

1. Local Media HQ
2. Growth In Reverse: Newsletter & Email Growth
3. New Media
4. The Creator Spotlight Podcast
5. Small Press, Big Ideas

How many episodes of 'LetterLand are there?

'LetterLand launched a year ago and published 42 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on 'LetterLand?

Recent guests on 'LetterLand include:

1. Taylor Craig
2. Tim from 1440
3. Heather Hunter
4. Matt Paulson
5. Rae Lambert
6. Dan Berk
7. Kaleigh Moore
8. Adam Ryan

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