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Tomisms

Tom Chavez

Lessons from the startup trenches

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Substack
PricingOnly free issuesPublishesWeekly
Issues95Founded3 years agoLast Issue10 days ago
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Latest Issues

Judgement is the whole job now

“To know what we think, to be masters of our own meaning, will make a solid foundation for great and weighty thought.” – Charles Peirce

The aesthetics of a pitch deck change over time, and the winners get copied to death. In the ‘80s it wa...

10 days ago
3
1

Vinod Khosla is right about your taxes

My Take:

A founder I put a modest check into just had his exit. It’s his first. I remember that feeling. Watching somebody who spent five years eating shit sandwiches and rolling the boulder up the hill finally stand on top of it never...

25 days ago
6
1

The Asshole Bet

My Take:

I promoted a guy into a consequential role at the exact moment he’d privately decided to leave. He took the job anyway, purely as leverage: a fresh title to wave at his next employer while he was already halfway out our door.

I...

a month ago
7

Your Customers Hate AI

There’s a place I like to call VC-Land. You will not find it on a map. Technically, it’s a state of mind, but I like to picture it as an actual physical place anyway. In VC-Land, there are no buildings, only spaces made entirely of glass so...

2 months ago
7
2

Wordsmiths, Rise Up

One of the most virtuosic people I know with AI studied creative writing at Sarah Lawrence. The other is a runaway success as a Hollywood showrunner.

They’ve both been told for the past four years that AI is going to imminently replace the...

2 months ago
8

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  • Tom Chavez

    Building data + AI companies for 30 years. (Since it was niche/nerdy.) Exits to Microsoft/Salesforce/LiveRamp. Currently running super{set}. Into: company building, hip-hop, ethical tech, philosophy, and finding better ways forward.

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