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Judgment
Reviewing a friend’s management dojo proposal made me realize that the hardest management lessons I learned were not about skills
Sep 6
•
Stephen Pao
1
1
Right on Track
A financial advisor check-in, a 1.7% overweight in risk-controlled assets, and why AI capex has us watching that number more closely
Aug 30
•
Stephen Pao
2
2
Not Forever, Just for a While (Part 2 of 2)
What it actually took to leave Silicon Valley in 2001, once the only plan I’d ever followed had run out
Aug 16
•
Stephen Pao
1
1
How my first three jobs wore on me (Part 1 of 2)
Oracle, Visioneer, and Latitude Communications were really different experiences that ultimately drew me away from Silicon Valley the first time
Aug 9
•
Stephen Pao
5
3
1
The Power Law Comes to Seattle
Why the $9.6 Billion Seahawks Sale Feels Completely Different to an Old Tech Operator and Childhood Fan
Jul 12
•
Stephen Pao
2
2
1
The Point of a Playbook
Why I think AI should strengthen organizational learning instead of bypassing it
Jul 11
•
Stephen Pao
2
2
The Fourth of July Grab Bag
This week’s mixed bag of good news, price hikes, and one good rant
Jul 5
•
Stephen Pao
1
Separating Meaning from Voice in Product Marketing
How AI enables a clearer division of responsibilities, and where that division breaks down
Mar 16
•
Stephen Pao
1
Vibe Coding in Practice
What building a real scheduling tool taught me
Mar 8
•
Stephen Pao
3
2
The Unreliable Assistant
Notes from the bleeding edge of AI deployment
Mar 2
•
Stephen Pao
1
Running OpenClaw AI
Three tradeoffs I did not expect
Feb 22
•
Stephen Pao
1
1
2
I Switched My Internet Provider
It Will Not Be Enough
Feb 15
•
Stephen Pao
1
5
1
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