Peter O'Leary

From Reagan Kid to Radicalized: A Gen Xer's Political Journey
I was a 12-year-old Republican at a Reagan rally. Forty years and a few fateful decisions later, here's how I got here.
 • Peter O'Leary
Two Ways to Get Robbed in San Francisco
Why I'm reinstalling my cameras, and what eight years of watching my street has taught me about the city's two very different car-break-in operations
 • Peter O'Leary
The Skill I Wish Someone Had Taught Me at 18
Forty years in tech taught me what actually makes a great salesperson - and my son's graduation is forcing me to figure out how to teach it to him
 • Peter O'Leary
Tech Bros Didn't Build Silicon Valley. Pokémon players did.
A ruined dinner party, a Pokémon convention, and the real history behind a term everyone thinks they understand
 • Peter O'Leary

August 2026

When the City Digs Up Your Street — and Then Tickets You For It
A month of construction chaos in Noe Valley, and the letter I just sent City Hall about it
 • Peter O'Leary
GitHub and Linear Are Out of Sync. In 2026, That Should Be Unacceptable.
Why keeping your product and engineering systems in sync should be a daily, automated habit — not an end-of-sprint scramble.
 • Peter O'Leary
We Are Staring Skynet in the Face
Forty years after The Terminator, the movie's backstory doesn't feel like fiction anymore.
 • Peter O'Leary
Trump Isn't Playing 3D Chess With Iran. He Might Not Be Playing Chess at All.
On leverage, angles, and the difference between negotiating a business deal and negotiating with a country that invented chess
 • Peter O'Leary
What Getting My Energy Back Taught Me About Motivation (and Depression in Men)
A few months of feeling like myself again, and why I think more men should ask a doctor about it.
 • Peter O'Leary
USS Doris Miller
Whatever You Call the Ship, Don’t Forget the Man
 • Peter O'Leary
The Devil Doesn’t Look Like You Think
Choose whose Will you follow on Earth
 • Peter O'Leary
What “Ripple” Taught Me About the Road I’m On
What is the big deal about the Grateful Dead anyway?
 • Peter O'Leary
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