About
We build the companies
we wish existed.
Whimsey Labs is an AI venture studio based in Bend, OR. We take the 0-to-1 phase — the messiest, most uncertain part of building a company — and make it repeatable.
Founder
Mike Ulin
CEO & Founder · Bend, OR
Mike has spent his career at the intersection of AI, product, and company building. He's been part of founding teams that raised over $78M and built AI systems that now underwrite more than $4 trillion in assets.
At Paxton AI, he was CTO and scaled a legal research platform to multi-million ARR in under a year. Before that, he spent eight years at ZestyAI building climate risk models now used by Berkshire Hathaway, Allstate, and other major carriers. He started his career at McKinsey.
linkedin.com/in/michaelulinPaxton AI
Co-Founder & CTO
Scaled a legal research platform to multi-million ARR in under a year. Led product and engineering from zero to institutional traction.
ZestyAI
Founding Team
Spent eight years building climate risk models that now underwrite $4T+ in assets for carriers including Berkshire Hathaway and Allstate.
McKinsey
Consultant
Strategy and operations work that shaped how we think about building repeatable systems at scale.
Track Record
Industry firsts. Built by this team.
First of its kind
Industry-first AI wildfire underwriting model
Z-FIRE™ · ZestyAI
Outperforms traditional models by 44×. Trusted by carriers insuring 40% of the CA homeowners market.
First of its kind
Industry-first AI hail model
Z-HAIL™ · ZestyAI
20× lift in loss ratio segmentation. Launched April 2023.
First of its kind
Industry-first generative AI legal citator
Paxton AI Citator · Paxton AI
94% accuracy on the Stanford Casehold benchmark (2,400 examples). Launched July 2024.
2024
Most Disruptive Company of the Year
Oregon Tech Awards (40th Annual)
Paxton AI
2025
Innovation in Knowledge Management
Legalweek Leaders in Tech Law
Paxton AI
2023
Entrepreneur Award
Emory University
Michael Ulin · Class of 2011
2013
Most Innovative Award
McKinsey & Company
Michael Ulin
How We Work
Five things we actually believe.
01
Evidence over authority
We trust data and lived experience over credentials and consensus. If we believe something, we can show our work.
02
Ship fast, learn faster
Speed is a feature. We build and validate in weeks, not quarters. Every product teaches us something we carry forward.
03
Signal over noise
No fluff, no theory. We stay focused on what actually moves the needle for the businesses we build and the clients we serve.
04
Compound everything
Every venture, every client, every experiment makes the next one better. We build systems that get more valuable over time.
05
Radical transparency
We build in public. No polish, no spin — just notes from inside the labs. The messy parts are often the most useful.
Want to work together?
Book an AI Strategy Review or get in touch about a custom engagement. Seed to Series B is our sweet spot.
See Our Services →