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Substack
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Beehiiv
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Stacked Marketer
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Marketbeat
Meta
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AI For X

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

PublishesWeeklyEpisodes48Foundeda 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 Adam Ryan, founder of Workweek, which just raised $17 million and officially became a ne... more

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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 Marco Fazio, who just announced the sale of his newsletter Latestly, and Jesse Watkins, ... more

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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 Young Money author Jack Raines & Techpresso founder Louis Corneloup.

Jack will share ho... more

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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

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Recent Guests

Brian D'Erario
Co-founder of Kerri, a B2B media holding company
Kerri
Episode: Meet the AI agent closing newsletter sponsorship deals
Marco Fazio
Founder of Latestly AI
Latestly AI
Episode: He scaled and exited a million dollar AI newsletter in 18 months
Jesse Watkins
Founder/voice behind Newsletter Conference, Media Enthusiast
Newsletter Conference, Media Enthusiast
Episode: He scaled and exited a million dollar AI newsletter in 18 months
Jack Raines
Author of Young Money; Associate at Slow Ventures
Slow Ventures / Young Money
Episode: List Size Doesn't Matter
Louis Corneloup
Founder of Techpresso
Techpresso
Episode: List Size Doesn't Matter
Kendall Baker
Head of Newsletters at Yahoo!
Yahoo!
Episode: Google Zero Means the Future of Media Is Newsletters
Chenell Basilio
Founder of Growth In Reverse
Growth In Reverse
Episode: Google Zero Means the Future of Media Is Newsletters
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

Hosts

Tyler Morin
Host of LetterLand; Chief Newsletter Officer
Louis Nicholls
Co-host of LetterLand

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Talking Points

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He scaled and exited a million dollar AI newsletter in 18 months
Q: Was an exit in mind from day one, or did it evolve over time?
An exit was part of the plan from the start; Marco describes starting with profitability focus and then scaling to an exit when timing aligned, aided by brokers and NDA-heavy conversations with buyers.
He scaled and exited a million dollar AI newsletter in 18 months
Q: What was your growth blueprint to reach nearly 200,000 subscribers in under 18 months?
The strategy combined broad, evergreen topics with action-based content, global geotargeting for advertisers, and a mix of CPC, CPL, and sponsorship revenue, along with leveraging platforms like Spark Loop and Beehive to drive targeted campaigns and fast profitability.
Meet the AI agent closing newsletter sponsorship deals
Q: What makes Kerri's AI agent Savant effective in closing sponsorship deals end-to-end?
Savant automates outreach by pulling signals from target companies, creates tailored email templates, runs A/B tests, and surfaces calls to action for the human seller, dramatically reducing time to close and enabling near real-time deal progression.
Meet the AI agent closing newsletter sponsorship deals
Q: What justifies Workweek's rapid fundraising and how does the new capital unlock the next phase?
The $17 million raise enables expansion of tooling, community-building features, and scaling to serve more creator communities across verticals, aiming to reach parity with larger players while maintaining focus on its unique creator segment.
Meet the AI agent closing newsletter sponsorship deals
Q: Do you see Workweek directly competing with Beehive and Substack, or is it a different product altogether?
Workweek is positioned as a platform that sits within professional networks and targets industry-specific creators, emphasizing workflows and monetization for niche audiences, while acknowledging competitive dynamics with Substack and Beehive but focusing on a different value proposition for a specific creator type.

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Frequently Asked Questions About 'LetterLand

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

This show centers on the evolving newsletter ecosystem, with hosts unpacking weekly moves, trends, and business models shaping newsletters as distribution channels and revenue engines. Episodes frequently feature practitioners and operators from the creator economy, advertising, and media, discussing topics like sponsorships, AI-assisted writing, onboarding flows, live events, and platform dynamics. Notable throughlines include the tension between creator independence and platform support, the rise of multi-channel monetization (ads, sponsorships, events, paid communities), and practical tactics for growing audiences, securing sponsors, and driving durable revenue. A few episodes spotlight big industry players or notable founders, but the f... more

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2. Local Media HQ
3. The Creator Spotlight Podcast
4. Small Press, Big Ideas
5. The Nathan Barry Show

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'LetterLand launched a year ago and published 48 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. Brian D'Erario
2. Marco Fazio
3. Jesse Watkins
4. Jack Raines
5. Louis Corneloup
6. Kendall Baker
7. Chenell Basilio
8. Nic Conley

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