'LetterLand

Letterland Live SPAM or STAR is powered by beehiiv. Want to send from the ESP where newsletter legends are made? Get 30% off beehiiv with code FALL30 @ beehiiv.link/fall30

This week on Letterland LIVE we're joined by Jimmy Pawelski, Head of Growth at TLDR (8M+ readers), and Kate Samuelson, co-founder of Cheapskate London and Senior Newsletter Editor at BBC Studios.

Jimmy's ChatGPT ads were getting cheap clicks, but those visitors weren't signing up. So he used Claude Code to match each landing page headline to the ad someone clicked, and saw a ~30% lift in subscriptions. Plus, we ask the question every operator wants answered: could you still build a TLDR in 2026, and where is growth coming from now?

Kate shares what she's brought from the BBC to Cheapskate London, her weekly guide to the city's best events, read by 60,000+ Londoners.

We'll also get into:

- Are newsletters cooked? Taylor Lorenz says she lost a third of her paid subscribers, and Kendall Baker fires back
- Gmail inbox placement fell from 91% to 82% this year, per Validity
- The UK's competition watchdog investigates Meta's new scraping terms
- Substack's update blitz: metered paywalls, freewalls, lists and... custom cursors
- Rowan Cheung's lessons from growing The Rundown to 3.5M subscribers
- 6AM City launches Southward, because 96% of its readers travel every year
- The Unsung Heroes Draft: Tyler and Louis each build a dream team
- Question of the Week: one great issue every two weeks, a good one 3x a week, or an OK one daily?

... 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.

Letterland Live SPAM or STAR is powered by beehiiv. Want to send from the ESP where newsletter legends are made? Get 30% off beehiiv with code FALL30 @ beehiiv.link/fall30

This week on Letterland LIVE we're joined by Jacob Donnelly, founder of A Media Operator, fresh off moderating the AMO Summit.

Jacob plays Spam or Star (Is fandom the only metric that matters? Should every paid newsletter also run ads?), shares his biggest takeaways and a little green room intel from the AMO Summit, tells us where he stands on the "newsletters are dead" debate, and reveals what he reads every day.

Then Jordan DiPietro, founder of Signal // Noise Media, operating partner at srch., and former CEO of The Hustle and Hampton. Jordan breaks down how to tell if you built an audience or just a relationship with an algorithm, his three creator arbitrages (attention, taste and trust), how he's growing and monetizing Signal // Noise, whether the $7-a-month tier is a dead end, and why media companies should still hire 22-year-olds.

We'll get into:

- Fans vs. readers: Industry Dive's Sean Griffey says Morning Brew lost its fandom, and Brew CEO Robert Dippell fires back
- Stratechery is now presented by Stripe, and paying subscribers can't skip the ads
- Happy 4th birthday, Feed Me
- Substack's app now drives 40%+ of new subscriptions
- Axios is launching products by job title, because that's how people prompt AI
- Consulting Hat: a $1M-a-year solo newsletter operator wants to grow faster
- Chris Koerner's $1.40 subscribers from an AI agent running his Facebook ads, why Matt McGarry says the single-ESP newsletter is dying, LinkedIn's longer "see more", and more actionable intel

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

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

Want some Pro Bono (Latin for "totally free, you guys") consulting from Tyler & Louis? Submit your most pressing newsletter questions here (https://forms.gle/uH6sAPMoTA4KXt7k7). Tyler & Louis could answer it live on air.

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

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.

Letterland Live SPAM or STAR is powered by beehiiv. Want to send from the ESP where newsletter legends are made? Get 30% off beehiiv with code FALL30 @ beehiiv.link/fall30

This week on Letterland LIVE we're joined by Ben Tossell, founder of Ben's Bites, the AI newsletter with 172,000+ subscribers.

Every's CEO Dan Shipper says the newsletter is dead because his AI agent reads his inbox now. Ben tells us if he's right, how he uses AI as a reader AND an operator, how his fund fits into the Ben's Bites business model, and whether Ben's Bites is about to become a video.

Then Milly Tamati, CEO & founder of Generalist World, a newsletter 55,000 people read each week, plays Spam or Star and breaks down if her social quiz growth hack is still working.

We'll get into:

- Gmail's AI Inbox comes to paid Workspace accounts
- "The newsletter is dead": Nathan May, Matt McGarry and Emily Sundberg react
- Marc Lou's MailCheap hits 3-figure MRR
- Workweek's B2B network: 39 newsletters, 23,651 subscribers, and why B2B's 3-5% creator budget is about to climb
- MarketBeat's $150 million in net income (40% in the last two years)
- Michael Burry's Substack price hike
- Consulting Hat: 3,000 hospital admins and a $150 placement. Is that the right price?
- Kill the logo in your ads, cut your signup form to one field, and more actionable intel
- Are you tapping Substack as a growth channel? Your answers

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

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

Want some Pro Bono (totally free) consulting from Tyler & Louis? Submit your most pressing newsletter questions here (https://forms.gle/uH6sAPMoTA4KXt7k7). Tyler & Louis could answer it live on air.

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

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.

Letterland Live SPAM or STAR is powered by beehiiv. Want to send from the ESP where newsletter legends are made? Get 30% off beehiiv with code FALL30 @ beehiiv.link/fall30

This week on Letterland LIVE we're joined by Hunter Kallay, founder of FryAI, a free daily AI newsletter with 50,000+ subscribers, and Publisher Partnerships Lead at SparkLoop.

Hunter breaks down the AI you can put to work in your newsletter right now.

Plus, Substack is having a moment. Should you join?

We'll get into:

- Substack's 3 new sponsorship formats: the upgrade, the unlock and the masthead
- Why Emily Sundberg says the "upgrade" could hurt publishers
- Zach Lowe brings The Lowe Post to Substack
- Is Threads about to add Substack to your profile?
- SponsorGauge, the new Yelp for newsletter sponsors
- Consulting Hat: can you add 3,000 subscribers from LinkedIn in 90 days?
- The daily newsletters operators never miss
- Do serious operators still track open rates?

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

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

Want some Pro Bono consulting? Submit your most pressing newsletter questions here (https://forms.gle/uH6sAPMoTA4KXt7k7). Tyler & Louis could answer it live on air.

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

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 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
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 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.

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.