Morning Brew just bought another newsletter. Who's next?
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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.
Subscribe to never miss a Letterland LIVE: youtube.com/@LetterlandLIVE
Follow the 'land on socials:
LinkedIn: 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.
30 Sept 2026
10,000 downloads in 3 hours: The Pour Over's app playbook
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:
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.
23 Sept 2026
Is a bot your best newsletter subscriber?
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.
Who has been a guest on 'LetterLand
Names identified in recent episode analyses. Showing up to five guests.
Gunnar Holm
TJ Larkin
Dan Barry
Jason Woodruff
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
YouTube views
11,389,462
Score snapshot 15 Sept 2025
Apple Podcasts (US)
5.0 / 5
2 ratings
Spotify
5.0 / 5
3 ratings
Podcast Authority Score: 69 / 100
A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.
Quality
88
Social presence
0
YouTube
93
Engagement
32
Contact 'LetterLand
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