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Is Gemini the new enemy at the inbox gate?

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Jan 17, 2026

Is Gemini the new enemy at the inbox gate?

👋 Hi Reader, My business runs on Google Workspace. I assume most of you running a newsletter reading this article are. I got a notification this week that Gmail is entering the Gemini era. Amongst the other Gemini-driven updates, what struck me is that Google is making email summaries aggregate at the inbox level in a new tab called ‘AI Inbox’. Official Gmail announcement on the Google Blog What do you mean? Jennifer Lawrence Laughing GIF by Sony Pictures Gmail has been showing email-level...

Substack and unfettered expression

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Jan 10, 2026

Substack and unfettered expression

👋 Hi Reader, I have spent an inordinate amount of time reading Matthew’s Substack ‘INTAKE’ series, and I absolutely adore what he has been writing about lately. But one issue - INTAKE#42 - during this holiday break has particularly piqued my interest. Matthew Rowean's INTAKE#42 on Substack I had this thesis that Substack creators had always used the medium as an outlet of expression, particularly on topics which mainstream media and socials might not fan the flames on in public. The more...

Cozying upto AI to compile your newsletter in 2026?

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Jan 3, 2026

Cozying upto AI to compile your newsletter in 2026?

👋 Hi Reader, Ryan Carr is an awesome guy. I happened to meet him last February in Austin, where I got to express my gratitude for the content he had been putting on Youtube. Along with Matt McGarry, he has created a helpful compilation of videos on how newsletter creators should think about their content strategy. The reason I bring up Ryan today, is he also frequently puts together amazing AI-centric tutorials. One of them happens to be creating entire newsletter content pieces with Claude -...

Acquiring LI subscribers, but crippled by reach? Here’s what to expect

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Dec 27, 2025

Acquiring LI subscribers, but crippled by reach? Here’s what to expect

👋 Hi Reader, I am a LinkedIn nut. I take all the arguments about LinkedIn being all cringe, AI-slop, broetry memes, and I raise you this: it is still the only social network I know, which insists on you showing up as your true self, not just a random handle ladiesman217. (10 points to you, if you caught the movie reference) So it follows that I spend an inordinate amount of time and effort understanding how the LinkedIn algo behaves. Which is when I realized that huge audience followership on...

Early Christmas for those starting local newsletters

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Dec 20, 2025

Early Christmas for those starting local newsletters

👋 Hi Reader, You know I am a sucker for seeing local businesses thrive. I never leave any stone unturned to cover helpful resources at the intersection of local businesses and newsletters. Since we are heading into downtime for the holiday season, I figure some of you are preparing hard and committing yourself to launch a local newsletter or media brand in 2026. If that’s a 'hell yes', you are in luck. I compiled 3 digital stocking stuffers from the best experienced local newsletter creators,...

Thy Substack cup of woe overfloweth

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Dec 13, 2025

Thy Substack cup of woe overfloweth

👋 Hi Reader, Seems like Substack newsletter creators cannot catch a break. The Substack platform has been rapidly making changes in 2025, and not of the good kind. First came paid subscriptions through the iOS app cutting paid earnings dramatically (we covered the paid subscription math in this LetterStack issue) Then came the shaky content moderation stance with a lot of questionable (absent?) decisions being made around moderating newsletters promoting hate speech. If you are curious about...

The Curious Case of Big Media Talent

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Dec 6, 2025

The Curious Case of Big Media Talent

👋 Hi Reader, If you recollect, I covered the phenomenon of ‘traditional media’ journalists jumping ship from their Big Media outlets to New Media avenues like newsletters, specifically Substack. I understand Big Media is watching this trend closely too and making amends to stem the talent exodus to newsletters. How are they exactly making amends? Well for starters, they are helping their crew build their own personal brand online. The Wall Street Journal is going the whole nine yards by...

Youtube mass bans (and what you could do about it)

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Nov 29, 2025

Youtube mass bans (and what you could do about it)

👋 Hi Reader, ICYMI, there has been a mass outcry on X over Youtube’s AI review decisions over entire Youtube channels getting wrongfully banned overnight at scale. Youtuber 'Norse797', who had over 100k subscribers and 25 million lifetime views on his YT channel covering aviation news, was served a ban by an automated Youtube decision mod. Seems serious, until you realize, the purported reasons were over his comments as a teen years ago on an alternate account. norse797 @bjr2730 YouTube...

A small gift for you inside (to express thanks)

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Nov 22, 2025

A small gift for you inside (to express thanks)

👋 Hi Reader, As you are well aware, I took over LetterStack less than a year ago as the present owner. I spent the last two decades building and launching products, but to be honest, no endeavour in my career gives me more joy than to write to you folks every Saturday. I know we are not a big community at this point, in fact, we are less than a thousand people. But the fact, that more than half of you open and devour the posts I send out every weekend, is immense motivation to show up, every...

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