About

Builds first. Advises second.

Whimsey is a one-person fractional AI leadership practice in Bend, Oregon. The practice works with no more than four active fractional clients, publishes its prices, and links every claim to a public source. Here’s the longer story.

Mike Ulin
Founder & CEO

Mike Ulin.

Mike has spent his career doing one thing in different costumes: teaching machines to price what experts said couldn’t be priced. At ZestyAI, eight years building climate-risk models — including the first AI wildfire underwriting model approved by a state insurance regulator — that now underwrite more than $4 trillion in assets for major national carriers. As co-founder and CTO of Paxton AI, he shipped the first generative-AI legal citator (94% on Stanford’s Casehold benchmark), raised $28M, and scaled it to multi-million ARR in under a year.

Before the founding years: McKinsey & Company (technology practice), the Federal Reserve Bank of Atlanta, and RPX Corporation — where he worked on the Rockstar/Nortel patent transaction. At PowerScout he built the first AI system to assess rooftop solar potential from satellite imagery, backed by a $1.5M U.S. Department of Energy award and featured twice by NVIDIA.

Four granted U.S. patents (they’re linked on the awards page — three are about hail, long story). Emory University’s 2023 Entrepreneur Award.

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FIG. 4 — SOLAR, FROM ORBIT · A STILL FROM THE HERO FILM ON THE FRONT PAGE
How We Work

Five things we actually believe.

These started as the Whimsey Labs operating principles, back when this was a venture studio. They survived the pivot because they were never really about ventures.

01Evidence over authority — we trust data and lived experience over credentials and consensus. If we believe something, we can show our work.
02Ship fast, learn faster — speed is a feature. We build and validate in weeks, not quarters.
03Signal over noise — no fluff, no theory. We stay on what actually moves the needle.
04Compound everything — every engagement makes the next one better. We build systems that appreciate.
05Radical transparency — published prices, a clear client limit, and weekly notes.

^Adapted from the original Whimsey Labs operating principles. Still true. Still practiced.

Track Record

Industry firsts, in order of appearance.

2016PowerScout — first AI system to assess rooftop solar potential remotely from satellite imagery. $1.5M DOE SunShot award; featured twice by NVIDIA.Clean energy
2019Z-FIRE™ · ZestyAI — first AI wildfire underwriting and pricing model; 44× better property-level risk prediction (per ZestyAI); approved by a state insurance regulator.Insurance
2023Z-HAIL™ · ZestyAI — first AI-powered hail model; 20× lift in loss-ratio segmentation (per ZestyAI).Insurance
2024Paxton AI Citator — first generative-AI legal citator; 94% on Stanford Casehold (2,400 examples).Legal
The full award & press record →