'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 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 r...

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 tel...

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 yo...

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 M...

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...

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," an...

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 dow...

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 a...

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 quali...

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...

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 wri...

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 "inde...

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 202...

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 want to talk to you, and what newsletter advertisers actually care about. We’ll also discuss: 💰 Daily Upside founder Patrick Trousdale steps down 🤖 Sub...

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: Substack's partnership with Panagram to fight AI slop, and beehiiv's new Community feature from its Summer Release event. We'll also get into: 📝 Beehiiv q...

Is the newsletter industry's favorite metric officially dead? This week on Letterland Live, Tyler Morin and Louis Nicholls break down the news out of France that could spell the end of email open rates as we know them — and what it means for how you measure your newsletter's success. Also in the rundown: major publishers are opting out of Google Search entirely, and The New York Times is going loc...

This week on Letterland LIVE we're joined by Taylor Craig, founder and CEO of Launch Live Now. Taylor helps media brands and creators launch live shows. We'll dig into why live is a massive blue ocean opportunity for newsletter operators, what actually makes a live show work, and how to find winning content formats. We'll also get into: 🤖 Sponsors are quietly blacklisting AI-heavy newsletters 📺...

This week on Letterland LIVE, we welcome 1440 founder and CEO Tim Huelskamp. Tim built 1440 into one of the biggest daily newsletters in the world. We'll get into the playbook behind scaling a daily news digest to millions of readers, the economics of the aggregation model, and where he sees opportunity in the newsletter space heading into the second half of 2026. We'll also get into: 📱 A new pla...

This week on Letterland LIVE we're joined by Growletter founder Matt McGarry and newsletter sponsorship strategist Heather Hunter. We're talking about the new kings of media, a huge AI opportunity for newsletters, and how to find love in the inbox. Plus everything else you need to know about the newsletter world. Subscribe to never miss a Letterland LIVE: https://www.youtube.com/@LetterlandLIVE Jo...

This week on Letterland LIVE we're joined by MarketBeat founder and CEO Matt Paulson and DNNR co-founder Rae Lambert. Matt is a legend of the finpub space who's grown MarketBeat to $60M+ in revenue. We'll get into how to keep your media business lean, whether starting a newsletter in 2026 is even worth it, and how many emails you should be sending subscribers. Rae founded DNNR in 2023 to help crea...

A newsletter just hit a $101M valuation, without raising a dime. We break down 1440's jaw-dropping numbers and what it means for the business of newsletters. We also discuss... 💰 The Rundown's first strategic investment 📬 The Flyover's $5M crowdfund 🐝 Inside beehiiv's rise to $30M ARR with employee #7 Daniel Berk 🔍 AEO strategist Kaleigh Moore breaks down AI search 📧 Our daily newsletter goes...

Do BuzzFeed, Business Insider, and other pageview/scale era media companies still have some life left in them? We chat with Industry Dive founder Sean Griffey about what everyone is missing in the pageview media model. We also discuss... 🍾 Workweek's Partner Platform launch with Adam Ryan 🔮 Substack's Once and Future Media Forum 🐝 Beehiiv's Summer Release Event ⛰️ Starter Story's starter story...

In this special holiday edition of LetterLand, Louis and Tyler look past 2025 to predict the massive shifts coming to the newsletter and creator economy in 2026. From the death of the "middle class" newsletter to the surprising B2B sales strategies borrowed from OnlyFans, they break down why the old playbooks are breaking and what will replace them. Follow Louis: https://x.com/louisnicholls_ Follo...

In this episode, Louis and Tyler sit down with Ryan Sager, co-founder of Who Sponsors Stuff , to break down how to monetize your newsletter through live events. We explain why you should stop chasing celebrity speakers and how to get sponsors to cover your costs before you spend a dime. Ryan also shares how a small dinner series evolved into a successful conference and the best way to validate you...

This week, Louis and Tyler examine how to convert social media followers directly into newsletter subscribers using DM automation, effectively bypassing the friction of traditional landing pages. They break down the mechanics of "borrowing" audiences from other creators, outline strategies for securing free recommendations through strategic interviews, and share tactical advice on using tools like...