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Dropping Out and Other Low-Risk Life Decisions
Risk has never been cheaper, yet commitment has never been harder. On the Thiel Fellowship, the dizziness of freedom, and Silicon Valley accidentally…
Apr 29
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What Could Happiness Cost—$10 Million?
Nov 19, 2025
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The Permanent Underclass Has Good GMAT Scores
Mar 11
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How To Spend Your 20s & 30s in the AI Era
Aug 20, 2025
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Stained to perfection
Sep 24, 2025
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Dear Diary
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Who's a better writer, AI or me?
We took the NYT's viral AI writing quiz and (surprise!) have many, many thoughts
Apr 8
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Artificial Whimsy
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Good Grief
Lessons on loss from a play about memory and a real goodbye
Jan 15
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Artificial Whimsy
16
2026 currents and countercurrents
What will you swim towards in the new year?
Dec 31, 2025
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Artificial Whimsy
Stanford GSB '26 | Essays on AI and other things...mostly other things ¯\_(ツ)_/¯
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Business & Culture
View all
Dropping Out and Other Low-Risk Life Decisions
Risk has never been cheaper, yet commitment has never been harder. On the Thiel Fellowship, the dizziness of freedom, and Silicon Valley accidentally…
Apr 29
•
Artificial Whimsy
83
8
9
The Permanent Underclass Has Good GMAT Scores
On credentials, Claude Code, and going swimming anyway
Mar 11
•
Artificial Whimsy
169
33
14
It be like WHAT sometimes
On the limits of meme-speak and why we don't just say what we really mean
Feb 4
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Artificial Whimsy
17
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The Personal Assistant in Your Pocket: What It Takes
Apple's Siri promised us a personal assistant in our pockets 15 years ago. Now in the age of agentic AI, that promise could finally come true, but only…
Oct 28, 2025
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Anna Barber
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Céline Vendler
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Advice Column
A Last-Minute Gift Guide for People Who (Mostly) Don’t Need More Stuff
December is a strange time of year.
Dec 18, 2025
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How To Spend Your 20s & 30s in the AI Era
YC told us how to spend our 20s in the AI era. We reflect on what we’ve learned from having actually spent our 20s in the AI era.
Aug 20, 2025
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Artificial Whimsy
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The Whimsical Guide to Writing Well
A practical and emotional guide to writing in the age of LLMs—we traverse the 9 circles of AI slop hell to remember why we write and how we might…
Aug 6, 2025
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Artificial Whimsy
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