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For Founders5 min

Checkmate

You are sitting with a hard decision and the people whose judgment you trust are not in the room, so you either overthink it alone or ask whoever happens to be around.

Launch Checkmate

For founders, PMs, anyone facing a tough decision

What it does

Pressure-test a decision against a board of sharp, distinct thinkers and hear how each of them would actually push back.

Currently

Live and browser-only with no signup to start. You pick advisors from a roster of 35 famous thinkers like Annie Duke, Gordon Ramsay, and Esther Perel, describe your situation, and get AI-generated responses written in each one's voice. The responses come from a model, so treat them as provocations to think with, not real advice from the actual people.

Recently shipped

  • Jun 2, 2026Shipped the simulated advisory board: pick famous thinkers and get responses in their voice.
  • Jun 15, 2026Reframed it to lead with picking your advisor first, with a grouped gallery and illustrated avatars.

How it's built

AI / LLMUses AISolo

How I built it

I built this because the best decisions I have made came from imagining how a few specific people would react, and I wanted that on demand instead of only when I could get them on the phone. You pick a board, lay out your situation, and each advisor pushes on it from their own angle, so you hear the disagreement before you commit. The decision I am proudest of was leading with the advisor pick: choosing who sits on your board is the fun part and the part that actually shapes the answer, so I put it first.

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