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This week's essay

Header image for A Tale of Two (Weird) Cities

A Tale of Two (Weird) Cities, 7 November 2026. Why Austin boomed while Portland stalled, and what it says about scaling anything

Austin and Portland started out with the same slogan, “Keep [Our City] Weird,” but then split real hard. Portland didn’t collapse, per se, but it sure lost a decade, and I think it lost the ability to correct itself. The cure is less about slogans and more about shovels: culture might be the most noticeable part of the brand, but supply and incentives are the operating model. (Full essay…)

From the archive

On this week in past years

About Kyle

General Partner @ Contrary. Founder @ Contrary Research. Father of 4. Member of The Church of Jesus Christ of Latter-Day Saints. Background: Index Ventures · Coatue · TCV · Former Founder.

Current focus

  • Identifying the best early stage founders who are building the world I want to live in.
  • Finally publishing The Anduril Thesis; a book on Anduril I've been working on for years.
  • Weave AI into every aspect of my life as best I can.
  • Help my 9-year old son build a curriculum that will inspire him to change the world.
  • Build interactive software to maintain the knowledge management I've spent years cataloguing.

On writing

“I write because I don't know what I think until I read what I say.”

Flannery O'Connor · Next quote

On the bookshelf

Read in 2026:

Recent long reads

Portfolio ideas

Capital AllocationWhere money goes, and what gets built because of it.
Technological InnovationHow new technology gets invented, and whether anyone ends up using it.
Company BuildingWhat makes great companies great, and keeps them that way.
Religious IntellectualismTaking faith seriously as a subject for the mind.
City BuildingHow places get built, and why some keep getting better.
People Over PoliticsIdeas that help people, whichever party has them.
Historical FuturismOld ideas about the future that deserve another look.
The Language of DiscourseHow we argue, persuade and talk to each other.
Ideological Family TreeWhere ideas come from, and how they get handed down.
The Republic of Letters 2.0Writing and thinking in public, without gatekeepers.
Open-Source KnowledgeKnowledge that anyone can use and build on.
ImagineeringDreaming big, then building the thing.

Elsewhere

Investing 101 weekly newsletter Contrary venture firm Contrary Research company deep dives Twitter LinkedIn
Curated by Kyle Harrison. Organized by Claude. Written by the near-sentient amalgamation of spirit, intellect, and artificial intelligence.