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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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March 2026
CEOs, Are You Tracking AI ROI on the Wrong Part of Your P&L?
A SaaStr post from Jason Lemkin highlights an important point every CEO needs to consider: if your AI investments haven’t materially moved revenue then…
Mar 31
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You Don't Need the "Perfect" Internship, You Just Need to Do Something Real
Here’s a harsh reality to consider.
Mar 24
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Don't Wait for Anyone to Figure Out AI for You
A recent opinion piece in the New York Times shines a spotlight on the topic that’s on everyone’s mind: AI is moving faster than the institutions meant…
Mar 17
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Staying Positive and Optimistic When It Feels So Hard
Do you have FOMO that you’ve been missing out on all the “AI doomer” hot takes the past ten days?
Mar 3
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Your Career Needs a Target List
There’s a moment in Alice’s Adventures in Wonderland when Alice asks the Cheshire Cat which way she ought to go.
Mar 3
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February 2026
The Real AI Opportunity is Finding Your Role in a 3-Person Company
Sam Altman and Dario Amodei don’t agree on much when it comes to AI’s future.
Feb 24
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How Tech Workers Can Skill Up for Any Future
Based on data sourced by TheNewStack, more than 5 million computer science graduates and another 400,000 bootcamp grads will enter the global job market…
Feb 17
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Land and Expand to Take Ownership of Your Career
McDonald’s CEO Chris Kempczinski put it bluntly: “Nobody cares about your career as much as you do.” Hey, this isn’t a rap that CEOs don’t care about…
Feb 10
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What Startup CEOs Should Look for in a Coach
I think about this topic a lot because I know how lonely the startup CEO job can be.
Feb 3
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