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Jenna Movsowitz, co-founder of CPG media brand Express Checkout, discusses its all-cash acquisition by Morning Brew and what it signals for newsletter M&A. Nathan May, founder of growth agency The Feed, shares a paid acquisition perspective on Meta ads, funnels, and scaling audiences. Plus, Piers Morgan’s paid newsletters, Substack’s legal defense fund, AI-powered media, and whether group chats are the next newsletter.

Nate Wells, Head of Business at The Pour Over, leads growth and strategy for the Christ-first news company. He shares the thinking behind its app launch, from audience testing and App Store momentum to memberships, prayer features, and trial conversions. The conversation also explores whether newsletters should become apps, SMS for faith-based content, AI’s impact on curated news, and closing that first major sponsorship.

Austin Tedesco, co-founder of Spur and former growth leader at Every and Substack, joins Brian Morrissey, media analyst and founder of The Rebooting. They explore whether newsletters have peaked, how AI agents could transform discovery and operations, and why media brands must become useful tools, not just reading products. They also discuss events, paywalls, niche expertise, and the rise of bots as subscribers.

Michael Kauffmann, founder of Catskill Crew, is rebuilding a Catskills hamlet through newsletters, businesses, housing, and community spaces. Jack Westerkamp, co-founder of advertising media company Breaking & Entering, explains why social-first brands still need email and how to turn followers into subscribers. They also explore local newsletter networks, premium memberships, media kits, AI-written content, and the future of independent media.

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.

Adam Ryan, Workweek founder and CEO, is building a platform for practitioner-creators and niche professional communities after raising $17 million. Brian D’Erario, Kerri Media co-founder and former Dow Jones, Morning Brew, and Payload operator, reveals how an AI agent sources prospects, drafts outreach, and closes newsletter sponsorships. They also explore Puck’s reported valuation, job-board monetization, AI’s limits in sales, and the future of events and paid intelligence.

Marco Fazio, serial bootstrapper who built and sold Latestly AI to ~$1M ARR and ~200k subscribers in 18 months. Jesse Watkins, newsletter operator and event organizer behind Who Sponsors Stuff and The Newsletter Conference. They dig into rapid audience scaling, revenue-first product design, international monetization tactics, event-driven community building, and practical tools and partnerships for fast growth.

Louis Corneloup, founder of Techpresso who builds AI-focused newsletters and growth systems, and Jack Raines, author of Young Money and Slow Ventures associate who writes on careers and money. They debate why list size may not set sponsorship price. They unpack welcome flows, newsletter-to-book paths, creator investing, AI watermarking backlash, and high-converting landing page tactics.

Chanel Basilio, founder of Growth in Reverse and newsletter growth researcher, shares blunt takes on onboarding, landing pages, and common growth mistakes. Kendall Baker, head of newsletters at Yahoo Sports and newsletter strategist, discusses why legacy media is leaning into newsletters and how to build publisher-backed newsletter networks. They dig into AI, inbox product plays, sponsorship integrations, and newsletter bundling.

Sean Ryan, founder of Rotary Digital and veteran newsletter operator, explains why sponsorships are tougher in 2026. Manny Reyes, founder of Bulletin Growth and Meta ads specialist, reveals the ad formats and creative hooks that actually grow newsletter audiences. Short takes on legal headlines and new product launches pepper the conversation.