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Join the Letterland Brief daily newsletter to keep on top of all the headlines and intelligence: letterlandlive.comThis 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/@LetterlandLIVEFollow the 'land on socials:LinkedIn: linkedin.com/company/letterlandliveX/Twitter: x.com/LetterlandLIVEAbout: 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=sharingJoin the Letterland Brief daily newsletter to keep on top of all the headlines and intelligence: letterlandlive.comThis 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/@LetterlandLIVEFollow the 'land on socials:LinkedIn: linkedin.com/company/letterlandliveX/Twitter: x.com/LetterlandLIVEAbout: 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=sharingThis 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.comSubscribe to never miss a Letterland LIVE: youtube.com/@LetterlandLIVEFollow the 'land on socials:LinkedIn: linkedin.com/company/letterlandliveX/Twitter: x.com/LetterlandLIVEAbout: 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.comThis 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/@LetterlandLIVEFollow the 'land on socials:LinkedIn: linkedin.com/company/letterlandliveX/Twitter: x.com/LetterlandLIVEAbout: 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.comThis 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/@LetterlandLIVEFollow the 'land on socials:LinkedIn: https://www.linkedin.com/company/letterlandliveX/Twitter: https://x.com/LetterlandLIVEAbout: 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 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🤖 Substack’s AI detection tool sparks industry-wide backlash✈️ Air Mail launches “The Scenic Route” newsletter🎯 Why you should be writing your newsletter for one person📆 Brian Morrisey announces TRB Audience Summit in NYC… and everything else you need to know about the newsletter world.Subscribe to never miss a Letterland LIVE: https://www.youtube.com/@LetterlandLIVEJoin the Letterland Brief daily newsletter to keep on top of all the headlines and thought leadership: letterlandlive.comFollow the ‘land on socials:LinkedIn: https://www.linkedin.com/company/letterlandliveX/Twitter: https://x.com/LetterlandLIVEAbout: Letterland is the front page of the newsletter industrial complex. Exclusive interviews, breaking news, and hot takes.

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 local with a newsletter pilot in the Twin Cities.Then we're joined by Nathan May, cofounder of The Feed Media, to talk about what finpub growth tactics can teach every newsletter operator, whether Gen Z and Gen Alpha creators are actually onboarding to newsletters, the Meta ad formats working for publishers right now, and why SMS might be the biggest opportunity (and risk) in the space.⏰ Live every Wednesday at 10AM ET on X, YouTube, and LinkedIn📬 Get the newsletter about newsletters: subscribe to the Letterland Daily Brief at letterland.live

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 player enters the newsletter arena😴 Inbox fatigue and the new newsletter survival rules📍 When does your newsletter become a "media company"?⺽The newsletter course gold rush hits mainstream🔐 Why media authentication genuinely sucks🍗 Food giveaways as a newsletter growth engine... and everything else you need to know about the newsletter world.Subscribe to never miss a Letterland LIVE: https://www.youtube.com/@LetterlandLIVEJoin the Letterland Brief daily newsletter to keep on top of all the headlines and thought leadership: letterlandlive.comFollow the 'land on socials:LinkedIn: https://www.linkedin.com/company/letterlandliveX/Twitter: https://x.com/LetterlandLIVEAbout: 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 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 creators and communities launch dinner clubs. We'll get her take on the value of IRL, how to run a successful event for your audience, and more.We'll also get into:💰 Substack launches ads🔍 Kit drops Subscriber Signals📉 Matt McGarry thinks energy is leaving newsletters💸 6AM City hits profitability⭕ Circle announces Circle AI... and everything else you need to know about the newsletter world.Subscribe to never miss a Letterland LIVE: https://www.youtube.com/@LetterlandLIVEJoin the Letterland Brief daily newsletter to keep on top of all the headlines and thought leadership: letterlandlive.comFollow the 'land on socials:LinkedIn: https://www.linkedin.com/company/letterlandliveX/Twitter: https://x.com/LetterlandLIVEAbout: Letterland is the front page of the newsletter industrial complex. Exclusive interviews, breaking news, and hot takes.

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🌍 Africa's biggest newsletter

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 your event ideas without losing money.Follow Louis: https://x.com/louisnicholls_Follow Tyler: https://x.com/JPMorinChaseSubscribe for more!

In this episode, Louis and Tyler sit down with Matt Paulson, founder of MarketBeat, to break down what it takes to build a $50M media company. We talk about why obsessing over cost per subscriber is killing your growth and reveal the exact metrics to focus on instead. Matt also shares how to generate $1.5M a month with SMS marketing and why niching down is actually bad advice for building a massive business.Find Matt at Marketbeat.com or on Twitter at https://x.com/MattPaulsonSDFollow Louis: https://x.com/louisnicholls_Follow Tyler: https://x.com/JPMorinChaseSubscribe for more!