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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Technology leadership, photography, tennis, and whatever else life throws my way.
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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