Young Money by Jack Raines
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The Late-20-Something's Professional Dilemma
On the pressure to figure out your "thing".
Jan 23, 2025
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Jack Raines
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The Cost of Apathy.
Modern life has a modern problem: we don't have to do anything.
Aug 6, 2024
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Jack Raines
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77
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The Opportunity Cost of Everything
Some thoughts on some things this fine Monday morning.
Jan 19, 2022
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Jack Raines
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Infinite Games
There's more to the game than winning it, you know.
Mar 2, 2023
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Jack Raines
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Some Advice for a 22-Year-Old Just Getting Started
Basically this is the blog post I wish I'd read in 2019.
Aug 22, 2023
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Jack Raines
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Essays
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Chapter 58: From India, with Love.
A week in India for Tanmaye's wedding. Highlights include sick outfits, Delhi Belly, five days of fun.
Dec 26, 2025
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Jack Raines
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Some thoughts on "Head of Narrative"
The hottest new job in Silicon Valley.
Dec 18, 2025
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Jack Raines
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5
What Are You Optimizing For?
On separating the means from the ends and avoiding the inertia trap.
Aug 22, 2025
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Jack Raines
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9
Okay, I wrote a book.
Is this thing on?
Jul 17, 2025
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28% Loaded.
Another trip around the sun. Some thoughts on saying goodbye to my mid-20s, going monk mode for a few months, etc.
Apr 7, 2025
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Jack Raines
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Investing in Creators.
The creator economy is dead, long live creators.
Feb 17, 2025
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Jack Raines
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5
The Late-20-Something's Professional Dilemma
On the pressure to figure out your "thing".
Jan 23, 2025
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Jack Raines
480
56
52
Factory Reset.
A new appreciation for South Georgia, a few other thoughts.
Dec 6, 2024
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Jack Raines
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9
You Only Have to Get Rich Once.
Hitting it big in the market is electrifying, but can you hold on to what you made?
Nov 21, 2024
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Jack Raines
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Some Thoughts on What Makes New York so Great.
I have, surprisingly, become New York City's biggest apologist.
Oct 17, 2024
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Jack Raines
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19
Status Games Rule Everything Around Me.
Everyone's chasing something.
Oct 3, 2024
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Jack Raines
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20
The Cost of Apathy.
Modern life has a modern problem: we don't have to do anything.
Aug 6, 2024
•
Jack Raines
973
77
192
Travel Blog
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Chapter 58: From India, with Love.
A week in India for Tanmaye's wedding. Highlights include sick outfits, Delhi Belly, five days of fun.
Dec 26, 2025
•
Jack Raines
48
8
Chapter 57: A Week in Tel Aviv
Tel Aviv, with friends! With a brief detour on entry.
Aug 15, 2025
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Jack Raines
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Chapter 56: RV Trip Out West
RV, with friends!
Oct 24, 2023
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Jack Raines
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Chapter 55: Summer in Spain
Ibiza, Mallorca, and Marbella!
Aug 23, 2023
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Jack Raines
Chapter 54: Colombia with Columbia, Part 2
Headed to South America with 300 of my closest friends!
May 21, 2023
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Jack Raines
Weekly Newsletter
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Elon Musk Did It Again
Plus: fake quantum company buys real chip company, and Murray Hill guy breaks Twitter.
Feb 3
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Jack Raines
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Financial Modeling Will Be Obsolete
Claude, Claude, Claude, and more Claude.
Jan 26
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Jack Raines
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Happy 2026, Let's Get This Bread
Ski trip in France and some thoughts on self-driving.
Jan 5
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Jack Raines
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India, Deep Work, and Some 2026 Goals
Brief weekly update between Christmas and New Years
Dec 29, 2025
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Jack Raines
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