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The Trip We Didn’t Take
A string of small interruptions, and what showed up in their place.
Sep 27
•
Stephen Pao
1
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
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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
Stage One
What getting the first stent was like
Aug 23
•
Stephen Pao
2
9
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
Remembering to Say “We”
How Marsha finally got me into marriage counseling in Seattle, and why the best tools got us only part way there
Aug 2
•
Stephen Pao
5
1
2
Retiring to Roche Harbor?
A great visiting spot but perhaps not a home
Jul 27
•
Stephen Pao
2
1
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
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