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When You Reach a Fork in the Road, Listen to Yogi
I just finished lunch with two recent high school graduates who both played on the high school team where I’ve been an assistant coach the last three…
Jul 8
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Enough of the Generalities - Get Something Done
I read another one of those AI-and-the-future-of-work pieces this week in the New York Times.
Jul 2
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June 2026
Ask the "What, Why, and How" Questions
Right now you probably have a dozen or more browser tabs open, an email inbox full of newsletters you don’t remember subscribing to, and a social media…
Jun 17
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Keep Doing Some Human Thinking and Learning
“Are you ready for the summer, are you ready for the fun?!”
Jun 9
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Focusing on Service, Humility, and Serendipty
I’m on a train traveling from Osaka to Yokohama, nearing the end of a two-week trip to Japan.
Jun 2
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May 2026
Can We Really Remove All the Managers?
The latest theme rippling through Silicon Valley and organizations is a belief that huge efficiencies and cost savings can be captured by removing…
May 26
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How I Lost My Weekend Working With Claude
“You’re right, that’s on me.” This may perhaps be my favorite Claude AI response.
May 19
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Why the Future Needs to Be Human to Human
I’ve been consuming too much AI-future content lately — the doomers, the optimists, and everyone in between.
May 11
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How CEOs Deploy AI to Amplify the Skills That Matter Most
Three weeks ago we considered the concept of “cognitive surrender”, specifically what happens when your team stops doing the hard work of thinking and…
May 5
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April 2026
Four Baseball Lessons Every Startup CEO Should Embrace
My brain is definitely in baseball mode right now.
Apr 28
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Walled Gardens Are Dead …Long Live Walled Gardens!
Perhaps no ethos embodies Silicon Valley more than the idea of “open source”, and its natural converse that argues “walled gardens” ultimately fail…
Apr 21
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Don't Cognitively Surrender Your Human Advantage
Ezra Klein’s recent essay in the New York Times (subscription required) outlines a phenomenon people should pay attention to.
Apr 14
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