'LetterLand

Epizódy

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  10,000 downloads in 3 hours: The Pour Over's app playbook 30.09.2026 1h 2min

  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 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 Wired to Front Office Sports are betting on apps again. We ask the question every operator is wondering: should your newsletter become an app?We'll also get into:- Inc.'s new media power rankings- Puck makes it official: RedBird invests at a $250M valuation- Why snail mail newsletters are having a moment- beehiiv's State of Enterprise report- Substack co-founder Hamish McKenzie is back- Rachel Karten: LinkedIn drove a huge amount of subs- Brian D'Erario's 3 ways to use AI to land sponsors- Consulting Hat: how do you close your first sponsor at 125K subs?... 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.
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  Is a bot your best newsletter subscriber? 23.09.2026 1h 4min

  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.
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  This local newsletter is rebuilding an entire town 16.09.2026 1h 3min

  Apply to the Letterland Live Social Media Manager role now: https://drive.google.com/file/d/1hOfhf3DPUJa-BTtZqxJW7f0fnCSMa9BV/view?usp=sharingThis 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 down why a camera-first media company needs email, how he turns a social following into subscribers, and what he'd do differently on day one if he were starting Breaking & Entering for a different industry today.Michael is monetizing a local newsletter in ways most operators have never dreamed of (think: literally rebuilding an entire town). He also walks through the network of local newsletters he's assembling to sell to national advertisers.We'll also get into:- Sam Parr is back in the newsletter game- Heatmap's revenue is up 115% year-to-date thanks to AI data centers- Tech journalist Alex Heath joins Sound Ventures as a VC partner- Ted Williams' plan to buy the Charlotte Observer back from hedge fund ownership for $5M- Media kits that actually close: Bay Area Times, TLDR, CFO Dive and Short Squeez- 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.
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  Google Deleted Your Domain Reputation. Now What? 09.09.2026 57min

  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.
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  Meet the AI agent closing newsletter sponsorship deals 02.09.2026 1h 2min

  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 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 quality across a network, and how Workweek works with sponsors.Brian breaks down how an AI agent is closing sponsorship deals for his newsletter.We'll also get into:- Puck is reportedly in talks to raise at a $250M valuation, roughly a 7x multiple on revenue- Matt McGarry's New Media Summit returns with Matt Paulson, Tyler Denk and Caleb Hammer- Mike Kaufmann is hiring a sales lead for his local newsletter aggregation play- Can you actually monetize a job board?- The WSJ AI op-ed backlash: is AI content any different than hiring a ghostwriter?- Matt Ragland on why you should pick your platform based on distribution, not features... 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.
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  He scaled and exited a million dollar AI newsletter in 18 months 26.08.2026 1h 3min

  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.
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  List Size Doesn't Matter 19.08.2026 1h 1min

  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 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 writing a book.Louis stops by to break down the welcome flow behind Techpresso: surveys, offers, and the mistakes that cost operators months.We'll also get into:- List size doesn't matter according to Sponsy's sponsorship pricing data- The backlash to Anthropic's AI watermarking (Ben Thompson is not a fan)- The two 17-year-olds whose finance newsletter has Wall Street hooked- The Economist sales page you should steal... 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.
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  Google Zero Means the Future of Media Is Newsletters 12.08.2026 53min

  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.
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  Sean Ryan on the brutal reality of newsletter monetization in 2026 05.08.2026 1h

  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 2026 and break down EXACTLY what's working on Meta.We'll also get into:🍺 Morning Brew is launching a beer with Montauk Brewing⚖️ eBay paid $56M to a newsletter its ex-CEO terrorized⚖️ Substack picked up the legal tab for Spy Talk's defamation suit🚀 TLDR launches a Hardware newsletter... 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.
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  State of the Newsletter Ad Market 29.07.2026 1h

  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.
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  Substack Declares War on AI Slop 22.07.2026 1h 1min

  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/@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.
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  Did France Just Kill Newsletter Open Rates? 15.07.2026 1h

  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
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  Smart Newsletter Operators Are Going Live in 2026 08.07.2026 1h

  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/@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.
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  The Contrarian Approach to a $100M Newsletter 01.07.2026 1h

  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.
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  The New Kings of Media – with Matt McGarry and Heather Hunter 24.06.2026 56min

  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/@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.
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  Substack breaks into the ad game, MarketBeat's Matt Paulson & DNNR founder Rae Lambert 17.06.2026 1h 2min

  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.
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  Can you build a $100M newsletter without investors? 10.06.2026 53min

  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)
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  Is everyone wrong about BuzzFeed? 03.06.2026 57min

  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
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  2026 newsletter predictions 05.01.2026 1h 3min

  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/JPMorinChaseSubscribe for more!
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  How to monetize a newsletter with events | ft. Ryan Sager of Who Sponsors Stuff 03.01.2026 33min

  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!