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Five Newsletter Recommendations

/ 2 min read

When it comes to the Internet, I have a “quick to subsribe, quick to unsubscribe” policy. This applies to Twitter, podcasts, newsletters, etc. Over time, some things rise to the top. Here are five newsletters that have survived that policy and that I read every time they hit my inbox.

Six at 6 on Sunday

A consistently great newsletter by a precocious Billy Oppenheimer, who is Ryan Holiday’s research assistant. He consistently produces an insightful and delightful newsletter every Sunday. No idea how he does this. He must read like a librarian on speed. Added bonus: I’ve had the honor of corresponding with him a bit, and he’s a very nice guy.

Sahil Bloom

Another totally precocious guy. Despite only being in his early 30s, Sahil’s newsletters are consistently full of sagely wisdom about life. Never not good. Again, no idea how he does this.


This is the flagship newsletter of a collection of newsletters that do a great job of summarizing the tech world each day. I also read the TLDR WebDev and TLDR Crypto newsletters every day.


Each week a small group of folks, led by the most interesting man on the internet, Kevin Kelly, recommend all manner of things ranging from products to websites to books. I never fail to find all kinds of off-beat and interesting stuff.


A delightful look at the world by a guy named Jono Hey. He has mastered the art of illustrating almost any concept in simple yet lovely drawings. I really enjoy how he can make stick figures look so expressive. I also recommend his new book “Big Ideas Little Pictures” which is a collection of his drawing and explanations.

Bonus Newsletter! Things that Occur to Me

A newsletter by yours truly. My brain conjures up the stangest things, and I decided to capture them and share them with you fine people.