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Your Customers Hate AI
And the loudest people in VC-Land have no idea. A field report from planet Earth.
Jun 25
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Tom Chavez
6
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Your Story is Your Moat
Feb 27
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Tom Chavez
8
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Forty Years of the Wrong Floor Plan
Feb 19
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Tom Chavez
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A Picnic of Shit Sandwiches
Apr 17
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Tom Chavez
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4
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Nixon's Wet Dream
Mar 19
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Tom Chavez
4
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Wordsmiths, Rise Up
AI was supposed to make writers obsolete. They turn out to be some of its most fluent operators. Update your funnel before the smart money beats you to…
Jun 11
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Two Prompts and a Polite Refusal
A Saturday-night demonstration of what AI safety actually does when somebody who wants something asks for it twice
Jun 4
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My Business That Almost Wasn't
In 2005 the green card showed up just in time. In 2026 it doesn't show up at all.
May 29
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Now Comes the Hard Part
Why every enterprise AI bet I'm watching get made right now is half a bet.
May 21
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Raise less. WAY less.
The cost of building a software company has collapsed 50–100x. Your round size hasn't caught up.
May 14
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Stay Fierce. Stay Sane.
5 habits of mind for the founder who has to do both.
Apr 24
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A Picnic of Shit Sandwiches
What six years of being early actually cost
Apr 17
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I Dated the Prom Queen
The statute of limitations on hard-earned lessons is collapsing.
Apr 2
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"They've Got This Handled"
The VC line that's killed more startups than a competitor ever could
Mar 26
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