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positioning

positioning

startups

+7

When your pipeline stalls, check which conversation you're having

May 4, 2026

•

3 min read

When your pipeline stalls, check which conversation you're having

Sales down 23% over 18 months — not for lack of customer contact, but for lack of the right kind of contact

Skipper Warson
Skipper Warson

startups

+7

"Um, shit," I said

Apr 18, 2026

•

2 min read

"Um, shit," I said

On echo chambers and the 1-pager I should have updated a year ago

Skipper Warson
Skipper Warson

product-market fit

+5

While I was gone... and then I realize I've been running experiments this whole time

Mar 29, 2026

•

7 min read

While I was gone... and then I realize I've been running experiments this whole time

On coming back, a domain detour, and the detective agency I never opened, but kinda did

Skipper Warson
Skipper Warson

product-market fit

+8

Why that feeling of "almost right but not quite" matters more than the perfect prompt

Nov 24, 2025

•

9 min read

Why that feeling of "almost right but not quite" matters more than the perfect prompt

AI is inevitably part of the conversation, here's what I've learned about when it actually helps — and when to trust your gut instead

Skipper Warson
Skipper Warson

How might we...

test what we think we know. How might we... stop building on assumptions we haven't tried out yet. How might we... know if what we're building is for the right person. Sensemaking at its finest from inside the work and sometimes from home.

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