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

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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 • Tom Chavez

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April 2026

Stay Fierce. Stay Sane.

5 habits of mind for the founder who has to do both.

Apr 24 • Tom Chavez

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A Picnic of Shit Sandwiches

What six years of being early actually cost

Apr 17 • Tom Chavez

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I Dated the Prom Queen

The statute of limitations on hard-earned lessons is collapsing.

Apr 2 • Tom Chavez

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March 2026

"They've Got This Handled"

The VC line that's killed more startups than a competitor ever could

Mar 26 • Tom Chavez

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Nixon's Wet Dream

A centralized database of every American. Fully searchable. No oversight.

Mar 19 • Tom Chavez

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The Engineer Said No

A Soviet bunker, a blackmailing AI, and the case for human doubt

Mar 12 • Tom Chavez

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What The Man Who Coined AI Knew That We Keep Forgetting

John McCarthy saw the wall that recursive self-improvement can't climb. Software is hitting it now.

Mar 6 • Tom Chavez

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February 2026

Your Story is Your Moat

A Conversation with Obama Speechwriter Terry Szuplat

Feb 27 • Tom Chavez

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Forty Years of the Wrong Floor Plan

What factory electrification teaches us about $285 billion in vanishing enterprise software value

Feb 19 • Tom Chavez

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Build vs. Buy Is Dead

There's a third path. And it changes who wins.

Feb 12 • Tom Chavez

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