$Architectural patent drawings behind Mike Ulin$

Fractional AI leadership from Mike Ulin

Your AI roadmap needs an owner.

Mike joins your leadership team to decide what to build, guide the people building it, and report progress to your board—without waiting for a full-time hire.

Talk AI with Mike

Free 30-minute working session. Bring the decision that keeps resurfacing.

Three-time founder · Four industry firsts · Four patents · $78M+ raised · $4T+ in assets underwritten

Mike Ulin, founder of Whimsey — **Mike Ulin**Three-time founder · Fractional CAIO

Proof

Mike has built the work he’ll lead.

He helped build the first state-regulator-approved AI wildfire underwriting model at ZestyAI, the first generative-AI legal citator at Paxton, and the first remote solar-assessment AI at PowerScout.

$78M+

Raised across his companies

$4T+

Assets underwritten by AI

Industry-first AI products

Patents granted^

Alumnus of

^More pending. Every claim on this page links to a live public source.

The Role

What Mike owns.

Whimsey is a one-person operating practice. Mike makes decisions with your team, guides delivery, and keeps leadership informed.

The roadmap and priorities

Choose the few AI projects worth doing, cost them, and document why they come first.

Build-versus-buy decisions

Test vendor claims, challenge estimates, and make the call with evidence your team can review.

Prototype and delivery

Turn the highest-priority idea into a working proof, then keep the build moving toward production.

Governance and board reporting

Put evaluation, security, legal review, and human escalation into the work from the start.

Team alignment and hiring

Keep the people doing the work aligned, and help define or hire an internal AI leader when the timing is right.

Mike’s work covered by

What We Build

What Mike can help you build.

Start with the business problem. The technology follows.

Find answers in company knowledge

Search documents and data, then return answers with the sources attached.

Automate multi-step work

Move a workflow from intake to result with checkpoints, evaluation, and an audit trail.

Handle customer conversations

Run intake, support, and scheduling by voice, with a clear handoff to a person.

Improve risk and pricing decisions

Build predictive models for underwriting, pricing, and risk.

Understand properties using imagery

Turn satellite and aerial images into property and location intelligence.

Lead the people building it

Scope the work, vet development teams, review estimates, and hold delivery to the plan.

Clients

Who does Whimsey work with?

You—if AI is tied to a real business decision.

Mike’s recent work spans AI startups, legal technology, insurance, climate risk, and property intelligence. The industries vary. The common thread is a consequential decision, valuable data, and a team ready to act.

Talk AI with Mike

AI foundersLaw firmsInvestment teamsInsurersBanksHealthcareIndustrial firms

How It Works

Five stages. One accountable leader.

The same method guides a focused proof of concept and an ongoing fractional leadership engagement.

Understand the goal

Define the decision, baseline, users, available data, and what a measurable win looks like.

Align the stakeholders

Name the sponsor, owner, users, technical team, and reviewers before the build starts.

Build the proof of concept

Test the core assumptions with representative data and the smallest useful working system.

Get feedback from real users

Put the system into real work and turn failures into the next evaluation set.

Refine and scale

Fix what failed, add operating controls, and expand the rollout in stages.

Read the full Whimsey method →

News & Awards

The proof never winks.

2025Innovation in Knowledge Management · WinnerLegalweek · Paxton AI

2024Most Disruptive Company of the Year · WinnerOregon Tech Awards · Paxton AI

2023Entrepreneur AwardEmory University · M. Ulin

2016SunShot Incubator Award · $1.5MU.S. Dept. of Energy · PowerScout

Full track record, every award, every article →

What you tell your board

“We brought on a fractional Chief AI Officer — the one who built the first regulator-approved AI wildfire model. He’s reviewed the roadmap, killed two projects, and prototyped the one that matters.”

Your next board meeting, roughly

FIG. 4 — solar rooftop patent plate, from the hero film

FIG. 4 — SOLAR, FROM ORBIT

Notes

We publish what we learn. No polish, no spin.

Build logs, vendor teardowns, and the occasional strong opinion — written the week it happened, not polished into a case study. Free, weekly-ish.

Read on Substack

Common Questions

Asked, answered, footnoted.

Do we need to share our code?

Only if you want codebase-level recommendations. We can work from product docs, user research, and roadmap conversations alone — code access enables deeper guidance but isn’t required.

What will Mike actually deliver?

A prioritized roadmap, clear build-versus-buy decisions, a working proof of concept for the highest-priority opportunity, governance for the work, and a cadence for keeping leadership informed. Ongoing engagements also include vendor evaluation, delivery oversight, and hiring support.

We’re a law firm. Can you work within our confidentiality rules?

Yes — the legal citator we built at Paxton lives under exactly those constraints. Engagement terms, data handling, and conflicts checks are all standard practice here, not an improvisation.

Can you manage our outsourced dev team?

Yes. Sourcing, vetting, and managing outside development teams is part of the engagement. We write specifications, review the work, and evaluate estimates.