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

PublishesWeeklyEpisodes45Foundeda year ago
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EntrepreneurshipBusinessMarketing

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Artwork for 'LetterLand

Latest Episodes

Join the Letterland Brief daily newsletter to keep on top of all the headlines and intelligence: letterlandlive.com

This week on Letterland LIVE we're joined by Yahoo! Sports' head of newsletters Kendall Baker & Growth In Reverse founder Chenell Bas... more

YouTube

This week on Letterland LIVE we're joined by Rotary Digital founder Sean Ryan and Boletin Growth founder Manny Reyes.

Sean's built an empire of brief, curated newsletters. We'll dig into whether that commitment to brevity helps or hurts monetization... more

YouTube

This week on Letterland LIVE we’re joined by Nic Conley, founder of The Follow Up.

Nic lives at the intersection of newsletters and sales. We’ll get into how important newsletter touchpoints are in the B2B sales process, when advertisers actually wa... more

YouTube

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

YouTube

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Accepts Guests
Accepts Sponsors
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New Media
New MediaMatt McGarry and Kolby Hatch
Growth In Reverse: Newsletter & Email Growth
Growth In Reverse: Newsletter & Email GrowthChenell Basilio and Dylan Redekop

Recent Guests

Nic Conley
Founder of The Follow Up
The Follow Up
Episode: State of the Newsletter Ad Market
Simon Owens
Media industry analyst and writer behind the Simon Owens Substack newsletter
Episode: Substack Declares War on AI Slop
Nathan May
Guest expert in newsletter monetization and meta ads
The Feed Media
Episode: Did France Just Kill Newsletter Open Rates?
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
Matt McGarry
Founder of Growletter
Growletter
Episode: The New Kings of Media – with Matt McGarry and Heather Hunter
Heather Hunter
Newsletter sponsorship strategist
Independent
Episode: The New Kings of Media – with Matt McGarry and Heather Hunter
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?

Hosts

Tyler Morin
Host of LetterLand
Louis Nicholls
Host of LetterLand

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Talking Points

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State of the Newsletter Ad Market
Q: What metrics matter when pitching advertisers in 2026?
Focus on the lead quality and lifecycle tracking rather than just open or click-through rates; present a clear narrative of where the lead came from, how they engaged, and how partnerships can be long-term rather than one-off buys. Case studies and demonstrated retention are highly persuasive.
State of the Newsletter Ad Market
Q: What is the playbook to close the first sales in a B2B newsletter?
Start with inbound lead forms to gather interested advertisers, then identify existing spend in similar newsletters and reach out to those brands, using your own list to find potential inroads and emphasizing a clear value proposition for why they should sponsor. Build a portfolio with strong case studies and be patient as you establish ad networks and partnerships.
Substack Declares War on AI Slop
Q: What do you think about Substack partnering with Panagram for AI-detection within the platform?
Simon provides a cautious, nuanced take: it's a public relations move that could help set norms, but the real value lies in how this tech is used to improve content quality without stifling creativity, and in recognizing the broader trend of content scrutiny online.
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.

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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. New Media
2. Local Media HQ
3. Growth In Reverse: Newsletter & Email Growth
4. The Creator Spotlight Podcast
5. Creator Science with Jay Clouse

How many episodes of 'LetterLand are there?

'LetterLand launched a year ago and published 45 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. Nic Conley
2. Simon Owens
3. Nathan May
4. Taylor Craig
5. Tim from 1440
6. Matt McGarry
7. Heather Hunter
8. Rae Lambert

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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