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Oliver Buchannon
Jacob Sky Levin
Top 1%

Apr 30, 2026

•

5 min read

Top 1%

A year of Inbox Hero 🎂

Jacob Sky Levin
Jacob Sky Levin
The Room Where it Happens

Apr 23, 2026

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4 min read

The Room Where it Happens

Ohio, access, and how quickly a door opens.

Jacob Sky Levin
Jacob Sky Levin
Moon Joy

Apr 16, 2026

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5 min read

Moon Joy

On splashdowns, sincerity, and the overview effect.

Jacob Sky Levin
Jacob Sky Levin
Find your Field

Apr 9, 2026

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8 min read

Find your Field

On nature and nurture.

Jacob Sky Levin
Jacob Sky Levin
Face Value

Apr 2, 2026

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12 min read

Face Value

How loneliness turned the human face into the most valuable asset in business.

Jacob Sky Levin
Jacob Sky Levin
Drop the Charade

Mar 26, 2026

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6 min read

Drop the Charade

On games, followers, and the art of looking stupid together.

Jacob Sky Levin
Jacob Sky Levin
The World's Dumbest Addiction

Mar 19, 2026

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10 min read

The World's Dumbest Addiction

Fruit-flavored poison, a rat utopia, and the hole we're trying to fill.

Jacob Sky Levin
Jacob Sky Levin
Based On

Mar 12, 2026

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7 min read

Based On

Thinking about standup, Shakespeare, and the death of authorship.

Jacob Sky Levin
Jacob Sky Levin
Supply Chain Risk

Mar 5, 2026

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5 min read

Supply Chain Risk

On Anthropic, the Pentagon, and who gets to draw the line.

Jacob Sky Levin
Jacob Sky Levin
The Monkey in the Machine

Feb 26, 2026

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12 min read

The Monkey in the Machine

The mechanics of virality, and why they're kept out of sight.

Jacob Sky Levin
Jacob Sky Levin
Manifest Destiny

Feb 19, 2026

•

10 min read

Manifest Destiny

Rewiring the brain without outsourcing it to the universe.

Jacob Sky Levin
Jacob Sky Levin
Betting on Everything

Feb 12, 2026

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10 min read

Betting on Everything

How uncertainty became America's newest consumer product.

Jacob Sky Levin
Jacob Sky Levin
Letter from an American (Consumer)

Feb 5, 2026

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8 min read

Letter from an American (Consumer)

On boycotts, attention, and our own impotence.

Jacob Sky Levin
Jacob Sky Levin
Lease Renewal

Jan 29, 2026

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8 min read

Lease Renewal

Running the numbers on a place.

Jacob Sky Levin
Jacob Sky Levin
Something in the Food

Jan 22, 2026

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11 min read

Something in the Food

Three weeks abroad left me suspicious of my own grocery store.

Jacob Sky Levin
Jacob Sky Levin
Breaking Point

Jan 15, 2026

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6 min read

Breaking Point

On comfort, complicity, and the line that doesn't exist.

Jacob Sky Levin
Jacob Sky Levin
Day For It

Jan 8, 2026

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7 min read

Day For It

How words and slang shape behavior, mood, and culture.

Jacob Sky Levin
Jacob Sky Levin
Down Under

Jan 1, 2026

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5 min read

Down Under

Observations from a functioning democracy.

Jacob Sky Levin
Jacob Sky Levin
Superforecasting

Dec 25, 2025

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11 min read

Superforecasting

Year-end rituals and the art of prediction.

Jacob Sky Levin
Jacob Sky Levin
Signal Loss

Dec 18, 2025

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10 min read

Signal Loss

How infinite content bankrupted our capacity to care.

Jacob Sky Levin
Jacob Sky Levin
Earners and Owners

Dec 11, 2025

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10 min read

Earners and Owners

The most important economic policy in a generation is rolling out this week.

Jacob Sky Levin
Jacob Sky Levin
The Solutionist's Dilemma

Dec 4, 2025

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7 min read

The Solutionist's Dilemma

Not every challenge is a problem in need of a fix.

Jacob Sky Levin
Jacob Sky Levin
Where are you from?

Nov 27, 2025

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6 min read

Where are you from?

Home, identity, and the interminable process of growing up.

Jacob Sky Levin
Jacob Sky Levin
Risk Capital

Nov 20, 2025

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11 min read

Risk Capital

Crying in the shower, the perverse incentives of venture capital, and why I'm hunting for founders as broken as I am.

Jacob Sky Levin
Jacob Sky Levin
Emergency Governance

Nov 13, 2025

•

14 min read

Emergency Governance

How gas station weed became the bargaining chip that ended a government shutdown.

Jacob Sky Levin
Jacob Sky Levin
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