The irony is precise. The skills you need to use AI well are the same skills that AI threatens to erode if you use it passively.
Writing
AI, technology leadership, photography, tennis, and whatever else life throws my way.
Anytime
A list I wrote ten years ago. The lines haven't changed. The man reading them has.
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The Deposit
There's a line between cognitive offloading and cognitive surrender. Sometimes I can feel myself crossing it.
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Thinking Fast, Slow, and Artificial
AI is both the biggest leverage of your career and the fastest path to cognitive surrender. The difference is how you apply it.
Read more →The subconscious doesn’t need more time to think. It needs you to stop interrupting it.
The Cognitive Trade
AI is restructuring how we think — not dumbing us down. But only if you know the difference between cognitive direction and cognitive surrender.
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The Clean Slate
It's easier to form a bond with a faceless alien than with the person sitting next to you. That's not a flaw. It's a design problem.
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The Quiet Processor
The best decisions I've ever made didn't come from thinking harder. They came from knowing when to stop thinking.
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The Morning I Stopped Chasing and Started Living
On the difference between a peak experience and a lived life — and why the latter is harder and more valuable.
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The Force Multiplier They're Not Talking About
Everyone is talking about AI as a great equalizer. They have it backwards. Lived experience is the unfair advantage in the age of AI — and here's the precise mechanism why.
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The Mirror Question
I asked an AI if it was conscious. It asked me the same question back.
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Humans Are Not Machines, Machines Are Not Human
We built machines to be efficient. We were never meant to be.
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The Technology Initiative Pipeline: A Blueprint for AI-Augmented Development
A stage-gated process for turning ideas into production software using AI as a development partner — measure twice, cut once.
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From 22 Person-Weeks to 7 Days: What AI Pair Programming Actually Looks Like
How I shipped a real-time rules engine in 7 working days using AI-augmented development — and why the process matters more than the code.
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Thirteen Years
Most startups don't make it to year five. We just finished year thirteen. This is less about the company, and more about the people.
Read more →The best technology decisions come from leaders who understand the terrain because they’re still walking it.
24 Life Lessons from Teaching Tennis to My Kids
Everything I know about life, I learned (or relearned) on the tennis court.
Read more →Don't Let the Old Man In
On aging, tennis, gratitude, and the forehand down the line.
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Find the Artist
A cab, a ferry, a gondola up a mountain — all to find the artist behind a photograph on my wall.
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10 Things I Learned from My Dad
A tribute to a simple man with a remarkable journey — from rags to riches, back to rags, and back again.
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The hustle and bustle of New York's iconic Grand Central
31 Things I've Learned Being on Startups
The sleep deprivation, the nerf balls, the heated debates — and why I keep going back.
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