'LetterLand

By Louis Nicholls, Tyler MorinBusiness Entrepreneurship Marketing

'LetterLand episodes

July 29 State of the Newsletter Ad Market
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/@LetterlandLIVE
Join the Letterland Brief daily newsletter to keep on top of all the headlines and thought leadership: letterlandlive.com
Follow the ‘land on socials:
LinkedIn: https://www.linkedin.com/company/letterlandlive
X/Twitter: https://x.com/LetterlandLIVE
About: Letterland is the front page of the newsletter industrial complex. Exclusive interviews, breaking news, and hot takes.
1 hr 1 min
July 22 Substack Declares War on AI Slop
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 quietly updates its Terms & Conditions
🎬 Alex Lieberman shares his Claude content machine on How I AI
💼 Matt McGarry gives LinkedIn newsletters another shot
🔒 Emily Kramer starts paywalling her AI marketing skills
... and everything else you need to know about the newsletter world.
Subscribe to never miss a Letterland LIVE: https://www.youtube.com/@LetterlandLIVE
Join the Letterland Brief daily newsletter to keep on top of all the headlines and thought leadership: letterlandlive.com
Follow the 'land on socials:
LinkedIn: https://www.linkedin.com/company/letterlandlive
X/Twitter: https://x.com/LetterlandLIVE
About: Letterland is the front page of the newsletter industrial complex. Exclusive interviews, breaking news, and hot takes.
1 hr 2 min
July 15 Did France Just Kill Newsletter Open Rates?
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
1 hr 1 min
July 08 Smart Newsletter Operators Are Going Live in 2026
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
📺 HubSpot's 70-person media machine reaches 50M people monthly
💳 Stripe is publishing book reviews — genius or content suicide?
📉 Substack's "$60K a year" income math doesn't add up
💰 The metric replacing CPL for smart publishers
📊 Trevor Hatfield says the newsletter ad model is about to break
... and everything else you need to know about the newsletter world.
Subscribe to never miss a Letterland LIVE: https://www.youtube.com/@LetterlandLIVE
Join the Letterland Brief daily newsletter to keep on top of all the headlines and thought leadership: letterlandlive.com
Follow the 'land on socials:
LinkedIn: https://www.linkedin.com/company/letterlandlive
X/Twitter: https://x.com/LetterlandLIVE
About: Letterland is the front page of the newsletter industrial complex. Exclusive interviews, breaking news, and hot takes.
1 hr 1 min
July 01 The Contrarian Approach to a $100M Newsletter
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/@LetterlandLIVE
Join the Letterland Brief daily newsletter to keep on top of all the headlines and thought leadership: letterlandlive.com
Follow the 'land on socials:
LinkedIn: https://www.linkedin.com/company/letterlandlive
X/Twitter: https://x.com/LetterlandLIVE
About: Letterland is the front page of the newsletter industrial complex. Exclusive interviews, breaking news, and hot takes.
1 hr 1 min
June 24 The New Kings of Media – with Matt McGarry and Heather Hunter
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
Join the Letterland Brief daily newsletter to keep on top of all the headlines and thought leadership: letterlandlive.com
Follow the 'land on socials:
LinkedIn: https://www.linkedin.com/company/letterlandlive
X/Twitter: https://x.com/LetterlandLIVE
About: Letterland is the front page of the newsletter industrial complex. Exclusive interviews, breaking news, and hot takes.
57 min
June 17 Substack breaks into the ad game, MarketBeat's Matt Paulson & DNNR founder Rae Lambert
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/@LetterlandLIVE
Join the Letterland Brief daily newsletter to keep on top of all the headlines and thought leadership: letterlandlive.com
Follow the 'land on socials:
LinkedIn: https://www.linkedin.com/company/letterlandlive
X/Twitter: https://x.com/LetterlandLIVE
About: Letterland is the front page of the newsletter industrial complex. Exclusive interviews, breaking news, and hot takes.
1 hr 3 min
June 10 Can you build a $100M newsletter without investors?
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 live TOMORROW (subscribe at letterland.live)
54 min
June 03 Is everyone wrong about BuzzFeed?
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
58 min
January 05 2026 newsletter predictions
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_
Follow Tyler: https://x.com/JPMorinChase
Subscribe for more!
1 hr 4 min