Essays

AI's Looming Talent Retention Problem

What happens when everyone gets too rich too fast to need to keep working?

May 4 • Jack Raines

Preorder Your Copy of Young Money, the Book!

Coming to a bookstore near you on August 4, 2026.

Apr 16 • Jack Raines

The trillion-dollar perception gap between Silicon Valley and normal people.

Maybe the real AI winners are the folks who just don't care?

Apr 9 • Jack Raines

Dispatch from the permanent underclass.

Come with me on a journey.

Apr 3 • Jack Raines

Check out Young Money, the Book.

Available everywhere you buy books, starting August 4th!

Mar 24 • Jack Raines

What Comes Next?

On anxiety, uncertainty, and all of this AI/professional angst.

Feb 9

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

Some thoughts on "Head of Narrative"

The hottest new job in Silicon Valley.

Dec 18, 2025 • Jack Raines

What Are You Optimizing For?

On separating the means from the ends and avoiding the inertia trap.

Aug 22, 2025 • Jack Raines

Okay, I wrote a book.

Is this thing on?

Jul 17, 2025

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 • Jack Raines

Investing in Creators.

The creator economy is dead, long live creators.

Feb 17, 2025 • Jack Raines

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