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The Looking Glass

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Essays on the endless journey of building products, teams, and ourselves.

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How to Stop Complaining About Your Software
September 9th, 2026•lg.substack.com
You Cannot Mandate an AI Transformation
September 1st, 2026•lg.substack.com
Eye, Hand, AI: a letter to my daughter
August 5th, 2026•lg.substack.com
How life was different during the early Internet
July 6th, 2026•lg.substack.com
To All the Folks Who Are About to Be Rich
June 13th, 2026•lg.substack.com
The Art and Excellence of Sales
June 9th, 2026•lg.substack.com
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I am an idiot
April 21st, 2026•lg.substack.com
How to Spot a World-Class Designer
April 14th, 2026•lg.substack.com
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What Excellent Growth Teams See That Others Miss
March 11th, 2026•lg.substack.com
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Playing Authentic Games
January 15th, 2026•lg.substack.com
The Lost Art of Crying
November 6th, 2025•lg.substack.com
Unsent Letter #25
September 16th, 2025•lg.substack.com
You're definitely going to be a manager now
September 9th, 2025•lg.substack.com
The Making of a Founder
August 21st, 2025•lg.substack.com
Unsent Letter #11
July 2nd, 2025•lg.substack.com
When AI Has Better Taste Than You
June 24th, 2025•lg.substack.com
Unsent letter #47
June 3rd, 2025•lg.substack.com