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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
•
Tom Chavez
6
2
2
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
•
Tom Chavez
8
1
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
•
Tom Chavez
4
1
May 2026
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
•
Tom Chavez
11
2
Now Comes the Hard Part
Why every enterprise AI bet I'm watching get made right now is half a bet.
May 21
•
Tom Chavez
6
3
3
Raise less. WAY less.
The cost of building a software company has collapsed 50–100x. Your round size hasn't caught up.
May 14
•
Tom Chavez
10
2
April 2026
Stay Fierce. Stay Sane.
5 habits of mind for the founder who has to do both.
Apr 24
•
Tom Chavez
6
1
A Picnic of Shit Sandwiches
What six years of being early actually cost
Apr 17
•
Tom Chavez
9
4
1
I Dated the Prom Queen
The statute of limitations on hard-earned lessons is collapsing.
Apr 2
•
Tom Chavez
4
1
March 2026
"They've Got This Handled"
The VC line that's killed more startups than a competitor ever could
Mar 26
•
Tom Chavez
6
1
Nixon's Wet Dream
A centralized database of every American. Fully searchable. No oversight.
Mar 19
•
Tom Chavez
4
1
The Engineer Said No
A Soviet bunker, a blackmailing AI, and the case for human doubt
Mar 12
•
Tom Chavez
3
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