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Letting Sleeping Dogs Lie
Part 3 of my overengineering saga, on the value of leaving well enough alone
Nov 8
•
Stephen Pao
1
I Gave My AI Its Own Account
A personal argument for giving AI a separate identity, a deliberately small slice of data, limited secrets, and payment credentials with hard…
Nov 1
•
Stephen Pao
1
1
1
Of Course, She Got Attached
A park dog, a fish named Fishy, and a family that can’t walk away
Oct 24
•
Stephen Pao
2
1
1
Poor Hank
A birthday gift, a secret adoption, and the cat who found his person
Oct 18
•
Stephen Pao
4
6
1
The Double Ten Grab Bag
I lost a best friend, and I’m still processing. A stent, healthcare, and payment apps clog my mind, too.
Oct 10
•
Stephen Pao
1
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A Partial Answer
My first consulting gig, and the drive back to California
Oct 4
•
Stephen Pao
The Trip We Didn’t Take
A string of small interruptions, and what showed up in their place.
Sep 27
•
Stephen Pao
2
3
Seven Months Off
What I actually did after quitting my job at AskMe to really reset
Sep 20
•
Stephen Pao
4
I Got Hacked
Even after a decade running an email security business, I personally fell for a device code phishing attack from my mom’s accountant with a real…
Sep 18
•
Stephen Pao
4
3
1
An Even Harder Enterprise Sale
AskMe tried to sell with a soft-dollar ROI during an economic downturn
Sep 13
•
Stephen Pao
2
An Unexpected Salvage Operation
Six weeks into my first new job after moving to Seattle, the Board asked me to figure out what to rescue from a business after letting go most of the…
Sep 12
•
Stephen Pao
2
2
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
Stage One
What getting the first stent was like
Aug 23
•
Stephen Pao
2
9
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