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My 5 Favorite Not Boring Essays of 2025

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With Christmas just two days away, and only one day to use the office printer to print very long documents, I wanted to share a few of my favorite not boring essays of the year. I’ve heard rumors, concerning and thus far unsubstantiated, that not every one of you has read every word of every essay this year; a week or two off should give you ample time to catch up. I have felt absurdly grateful that I get to do what I do this year, and it’s because you are willing to follow me down weird and seemingly disconnected rabbit holes, to great depths, wherever my curiosity leads. 2026 is going to be bigger and better. I have some fun things planned, including the biggest launch in not boring history since the newsletter started. I’m giddy. Thank you, and I hope you all have a joyful holiday season. Let’s get to it. If you are a fintech, you cannot move fast and break things like most tech startups. Things need to be solid: underwriting, processing, infrastructure, and integrations. Moving mon

My 5 Favorite Not Boring Essays of 2025 Electric Slide, Means & Meaning, Cable Caballero, Most Human Wins, Great Differentiation Dec 23, 2025 112 11 5 Share Hi friends 🎅, Happy Tuesday! With Christmas just two days away, and only one day to use the office printer to print very long documents, I wanted to share a few of my favorite not boring essays of the year. I’ve heard rumors, concerning and thus far unsubstantiated, that not every one of you has read every word of every essay this year; a week or two off should give you ample time to catch up. I have felt absurdly grateful that I get to d

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