'LetterLand

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 Jenna Movsowitz, co-founder of Express Checkout, which was just acquired by Morning Brew, and Nathan May, founder of The Feed.

Jenna and co-founder Nate Rosen started Express Checkout as a weekly CPG newsletter nearly four years ago. Now Morning Brew has bought it in an all-cash deal, its second acquisition this year. We ask the question every operator wants answered: is newsletter M&A heating up?

Nathan spends $2M a month on Meta ads across his clients. He breaks down what newsletter operators get wrong about paid growth, then stays on to do some pro bono consulting work.

We'll also get into:

- Piers Morgan's Uncensored goes paid with 4 newsletters on beehiiv
- Morning Brew president Devin Emery steps down
- A CEO sued a Substack writer and lost. Here's where the $240K goes
- Steal This: Vanessa Van Edwards' one-question trick for getting replies
- Google killed its domain reputation score, so build your own
- Emily Sundberg on why group texts could be the next newsletter
- Consulting Hat: "My newsletter doesn't bring in clients. Should I stop sending?"

... and everything else you need to know about the newsletter world.

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Follow the 'land on socials:
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About: Letterland is the front page of the newsletter industrial complex. Exclusive interviews, breaking news, and hot takes.

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 Nate Wells, Head of Business at The Pour Over, the politically neutral, Christ-first news company that just launched an app.

Within days of launch, The Pour Over app rocketed up the App Store charts. And they're not alone. Publishers from Wired to Front Office Sports are betting on apps again. We ask the question every operator is wondering: should your newsletter become an app?

We'll also get into:

- Inc.'s new media power rankings
- Puck makes it official: RedBird invests at a $250M valuation
- Why snail mail newsletters are having a moment
- beehiiv's State of Enterprise report
- Substack co-founder Hamish McKenzie is back
- Rachel Karten: LinkedIn drove a huge amount of subs
- Brian D'Erario's 3 ways to use AI to land sponsors
- Consulting Hat: how do you close your first sponsor at 125K subs?

... and everything else you need to know about the newsletter world.

Subscribe to never miss a Letterland LIVE: youtube.com/@LetterlandLIVE

Follow the 'land on socials:
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About: Letterland is the front page of the newsletter industrial complex. Exclusive interviews, breaking news, and hot takes.

Apply to the Letterland Live Social Media Manager role now: https://drive.google.com/file/d/1hOfhf3DPUJa-BTtZqxJW7f0fnCSMa9BV/view?usp=sharing

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 Austin Tedesco, co-founder of Spur, a new "growth agency and product lab for media founders," and Brian Morrissey, founder of The Rebooting.

Austin tells us all about Spur, the business he's building with Catherine Valentine after leading growth at Every and business development at Substack.

Brian recaps last week's TRB Audience Summit.

We'll also get into:

- Semafor's Max Tani says we've hit "peak newsletter"
- Business Insider goes all in on newsletters with Small Business Insider and VC Insider, its first paid newsletter
- Strategy Breakdowns' Tom Alder turns his newsletter into a product studio with Quicker
- Jason Calacanis is selling Inside.com
- Michael Blau's stock market brief built for your AI agent
- Aakash Gupta's paywall playbook: the info is free, the how-to is paid
- Dan Oshinsky on why your readers don't always know what they want
- Kaleigh Moore: get "very, very uncomfortably specific" about your niche

... and everything else you need to know about the newsletter world.

Subscribe to never miss a Letterland LIVE: youtube.com/@LetterlandLIVE

Follow the 'land on socials:
LinkedIn: linkedin.com/company/letterlandlive
X/Twitter: x.com/LetterlandLIVE

About: Letterland is the front page of the newsletter industrial complex. Exclusive interviews, breaking news, and hot takes.

Apply to the Letterland Live Social Media Manager role now: https://drive.google.com/file/d/1hOfhf3DPUJa-BTtZqxJW7f0fnCSMa9BV/view?usp=sharing

This week on Letterland LIVE we're joined by Jack Westerkamp, co-founder of Breaking & Entering, and Michael Kauffmann, founder of Catskill Crew.

Jack runs a daily live show about the ad industry and recently revamped B&E's newsletter. He breaks down why a camera-first media company needs email, how he turns a social following into subscribers, and what he'd do differently on day one if he were starting Breaking & Entering for a different industry today.

Michael is monetizing a local newsletter in ways most operators have never dreamed of (think: literally rebuilding an entire town). He also walks through the network of local newsletters he's assembling to sell to national advertisers.

We'll also get into:

- Sam Parr is back in the newsletter game
- Heatmap's revenue is up 115% year-to-date thanks to AI data centers
- Tech journalist Alex Heath joins Sound Ventures as a VC partner
- Ted Williams' plan to buy the Charlotte Observer back from hedge fund ownership for $5M
- Media kits that actually close: Bay Area Times, TLDR, CFO Dive and Short Squeez
- Is AI-written content any different from hiring a ghostwriter?

... and everything else you need to know about the newsletter world.

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

Subscribe to never miss a Letterland LIVE: youtube.com/@LetterlandLIVE

Follow the 'land on socials:
LinkedIn: linkedin.com/company/letterlandlive
X/Twitter: x.com/LetterlandLIVE

About: Letterland is the front page of the newsletter industrial complex. Exclusive interviews, breaking news, and hot takes.

Apply to the Letterland Live Social Media Manger role now: https://drive.google.com/file/d/1hOfhf3DPUJa-BTtZqxJW7f0fnCSMa9BV/view?usp=sharing

This week on Letterland LIVE we're joined by Justin Moore, founder of Sponsor Magnet, and Chris Miquel, founder of Audience Bridge.

Justin shows exactly how newsletters are still landing massive brand deals in 2026, why he built Sponsor Mole, how operators are using it, and the sponsorship money most newsletters are sleeping on.

Chris sets the record straight on deliverability: Google Postmaster Tools V1 is gone, your domain reputation went with it, and there's now a middleman reading your email that isn't human. He tells us what the AI inbox actually looks like and how to prep for it now.

We'll also get into:

- Letterland Live is hiring a social media manager
- Alex Hormozi hijacking Canva's domain with a "A design has been shared with you!" send
- Letterhead's 5 reader types, and why ghosts are a "deliverability tax"
- Adam Ryan: "We now have more HR newsletters on Safe Space than all of Substack"
- Media kits that actually close featuring Bay Area Times, TLDR, CFO Dive, Short Squeez
- How The Assist spends $3 a subscriber and has it all back within 7 days
- Is AI-written content any different from hiring a ghostwriter?

... and everything else you need to know about the newsletter world.

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

Subscribe to never miss a Letterland LIVE: youtube.com/@LetterlandLIVE

Follow the 'land on socials:
LinkedIn: linkedin.com/company/letterlandlive
X/Twitter: x.com/LetterlandLIVE

About: Letterland is the front page of the newsletter industrial complex. Exclusive interviews, breaking news, and hot takes.

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 newsletter platform, and Brian D'Erario, founder of Kerri Media.

Adam walks through the newsletter opportunity he's betting on, how he controls for quality across a network, and how Workweek works with sponsors.

Brian breaks down how an AI agent is closing sponsorship deals for his newsletter.

We'll also get into:

- Puck is reportedly in talks to raise at a $250M valuation, roughly a 7x multiple on revenue
- Matt McGarry's New Media Summit returns with Matt Paulson, Tyler Denk and Caleb Hammer
- Mike Kaufmann is hiring a sales lead for his local newsletter aggregation play
- Can you actually monetize a job board?
- The WSJ AI op-ed backlash: is AI content any different than hiring a ghostwriter?
- Matt Ragland on why you should pick your platform based on distribution, not features

... and everything else you need to know about the newsletter world.

Subscribe to never miss a Letterland LIVE: youtube.com/@LetterlandLIVE

Follow the 'land on socials:
LinkedIn: linkedin.com/company/letterlandlive
X/Twitter: x.com/LetterlandLIVE

About: Letterland is the front page of the newsletter industrial complex. Exclusive interviews, breaking news, and hot takes.

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, founder of Who Sponsors Stuff and The Newsletter Conference.

Marco grew Latestly to a $1M newsletter in just 18 months by turning every new signup into revenue. We ask the question every operator wants answered: how?

Jesse breaks down how newsletter operators need to be thinking about IRL events.

We'll also get into:

- Jack Conte's new Patreon and his pitch for a "better internet"
- Google Postmaster Tools V1 is dead
- The Economist is building an AI-personalized "For You" newsletter
- Sam Altman on why he refuses to let AI touch his inbox
- InsideHook's big swing: new editor, more original content
- Sean Griffey on why reciprocity is the real S-tier of engagement

... and everything else you need to know about the newsletter world.

Subscribe to never miss a Letterland LIVE: youtube.com/@LetterlandLIVE

Follow the 'land on socials:
LinkedIn: linkedin.com/company/letterlandlive
X/Twitter: x.com/LetterlandLIVE

About: Letterland is the front page of the newsletter industrial complex. Exclusive interviews, breaking news, and hot takes.

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 how a newsletter turned into a book deal (and a job investing in creators at Slow Ventures), plus whether anyone starting today should even bother writing a book.

Louis stops by to break down the welcome flow behind Techpresso: surveys, offers, and the mistakes that cost operators months.

We'll also get into:

- List size doesn't matter according to Sponsy's sponsorship pricing data
- The backlash to Anthropic's AI watermarking (Ben Thompson is not a fan)
- The two 17-year-olds whose finance newsletter has Wall Street hooked
- The Economist sales page you should steal

... and everything else you need to know about the newsletter world.

Subscribe to never miss a Letterland LIVE: youtube.com/@LetterlandLIVE

Follow the 'land on socials:
LinkedIn: linkedin.com/company/letterlandlive
X/Twitter: x.com/LetterlandLIVE

About: Letterland is the front page of the newsletter industrial complex. Exclusive interviews, breaking news, and hot takes.

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 Basilio.

Kendall will share his thoughts on why newsletters have never been more important for legacy media players and how to build a roster of "independent" newsletter operators.

Chenell stops by to drop some truth bombs about the common growth mistakes beginner newsletter creators make.

We'll also get into:

- Spotify, X, and Youtube moving the goalposts on creators
- The top newsletters startups pay for
- Apple is killing preview texts
- A killer sponsorship integration from Secret CFO that you should steal

... and everything else you need to know about the newsletter world.

Subscribe to never miss a Letterland LIVE: https://www.youtube.com/@LetterlandLIVE

Follow the 'land on socials:
LinkedIn: https://www.linkedin.com/company/letterlandlive
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About: Letterland is the front page of the newsletter industrial complex. Exclusive interviews, breaking news, and hot takes.

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, and if the rumors of newsletter monetization's demise are greatly exaggerated. 

Manny joins us to set the record straight on newsletter growth in 2026 and break down EXACTLY what's working on Meta.

We'll also get into:

🍺 Morning Brew is launching a beer with Montauk Brewing
⚖️ eBay paid $56M to a newsletter its ex-CEO terrorized
⚖️ Substack picked up the legal tab for Spy Talk's defamation suit
🚀 TLDR launches a Hardware newsletter

... and everything else you need to know about the newsletter world.

Subscribe to never miss a Letterland LIVE: https://www.youtube.com/@LetterlandLIVE

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

Follow the 'land on socials:
LinkedIn: https://www.linkedin.com/company/letterlandlive
X/Twitter: https://x.com/LetterlandLIVE

About: Letterland is the front page of the newsletter industrial complex. Exclusive interviews, breaking news, and hot takes.