All Episodes
Meet the AI agent closing newsletter sponsorship deals
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 R...
He scaled and exited a million dollar AI newsletter in 18 months
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 ...
List Size Doesn't Matter
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 ...
Google Zero Means the Future of Media Is Newsletters
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!...
Sean Ryan on the brutal reality of newsletter monetization in 2026
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 newslett...
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...
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...
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...
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...
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 ...
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...
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 ...
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 d...
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 wh...
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 ...
How to monetize a newsletter with events | ft. Ryan Sager of Who Sponsors Stuff
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 expl...
Q&A: Free ways to grow a newsletter (and more listener questions)
This week, Louis and Tyler examine how to convert social media followers directly into newsletter subscribers using DM automation, effectively bypassing the friction o...
What everyone gets wrong about newsletter growth — with Matt Paulson, Marketbeat
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 obsess...