Whimsey^ · Fractional AI Leadership

A three-time AI founder on yourlucky^leadership team. Fractionally.

Fractional Chief AI Officer for AI companies, law firms, and private equity. Four industry-first AI products. Four patents. $78M+ raised, and models that quietly underwrite $4T+ in assets. One seat opens this quarter.

^Serious about the work. Unserious about almost everything else.

Filmed in ink · 40 seconds
$78M+
Raised across his companies
$4T+
Assets underwritten by AI
4
Industry-first AI products
4
Patents granted^
Alumnus of
McKinsey & CompanyFederal ReserveRPXCox CommunicationsCDWIberdrolaZestyAIPaxtonMcKinsey & CompanyFederal ReserveRPXCox CommunicationsCDWIberdrolaZestyAIPaxton

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

The Alternative

You could hire a Chief AI Officer.

The hire

Six months of searching. $400K+ in comp. And a market where every résumé says “AI leader” — so the mis-hire rate is a coin flip your board gets to watch.

The rental

Same seat at your table, run by someone who’s shipped four industry-first AI products. A fifth of the cost. Quarterly terms. A track record you can click on.
Against the Field

Most fractional CAIOs are consultants. This one ships.

The fractional-CAIO market runs $2–8K a month and is mostly career advisors and prompt-course graduates. The vetting question buyers are told to ask is “show me what you’ve shipped.” Here’s the side-by-side.

The typical fractional CAIOwhimsey^
Shipped AI productsAdvisory track recordFour industry firsts — wildfire, hail, legal citator, solar
PatentsNone on recordFour granted — numbered and linked on the awards page
Diagnostic deliverableA slide deckA working prototype + roadmap, guaranteed
Regulator scrutiny survivedNot attemptedState insurance regulator approved underwriting model
Pricing“Book a call”Printed on this page
Engagement structureHours-based advisoryOutcome-structured — named 90-day deliverables, board cadence
Concurrent clientsAs many as possibleFour seats — counted, capped, public
What Changes

When the seat is filled.

01An AI roadmap you can defend to your board — prioritized, costed, with the reasoning shownStrategy
02Build-vs-buy calls made with receipts — from someone who has shipped both answersJudgment
03Vendors vetted by someone they can’t dazzle — demos decoded, pricing challenged, claims testedProtection
04Hiring help until you don’t need us — we’ll interview your Head of AI candidates, and tell you if you don’t need oneExit plan
What We Build

The projects the seat covers.

RAGRetrieval-augmented generation — search and answers over your own documents and data, with citations that hold up. The Paxton citator was this, at 94% on Stanford Casehold.Build or fix
AGENTSAgentic systems — AI that does multi-step work end-to-end with guardrails, evals, and an audit trail, not a chatbot with ambitions.Design & ship
VOICEVoice AI — intake, support, and scheduling agents that sound right, know their limits, and hand off before they embarrass you.Pilot to prod
MLMachine-learning & predictive models — underwriting-grade scoring, pricing, and risk models. The $4T-in-assets kind.Model to margin
GEOGIS, geospatial analysis & computer vision — satellite and aerial imagery models, property intelligence, and mapping pipelines. PowerScout and the ZestyAI models were exactly this, at $4T scale.Imagery to answers
TEAMSOutsourced & offshore build teams — we source them, vet them, manage them, and referee their estimates. Your budget stops being a rounding error in someone else’s favor.Source & manage
Who Sits Across the Table

Four kinds of clients. One seat.

AI founders

Seed to Series B. You need to know exactly what to build with AI, then ship it — with a roadmap your board can hold you to.

Book a free strategy session →

Law firms

AI adoption without the malpractice headlines — vendor vetting, workflow selection, and rollout, from the CTO who built the first generative-AI legal citator (94% on Stanford Casehold).

Book a free strategy session →

Private equity

AI diligence on targets and AI value-creation across the portfolio — judged with the same underwriting discipline that prices $4T in insured assets.

Book a free strategy session →

Other firms

Insurers, banks, healthcare, industrials — anywhere proprietary data meets a decision worth automating. If the problem is real, the vertical is negotiable.

Book a free strategy session →
How It Works

Three steps.

01

The Strategy Session

A free 30-minute call — and not a sales call. No pitch. Bring your roadmap, a vendor’s proposal, or the board question that keeps resurfacing. You leave with a straight answer either way, whether or not we ever work together.

Free · 30 minutes
02

The Field Report

Two weeks, fixed scope: a prioritized AI roadmap, a competitor teardown, and a working prototype of your top feature — so the plan is proven before you commit to anything bigger. Recorded walkthrough included.

Fixed price · Two weeks
03

Fractional Chief AI Officer

First 90 days: a costed AI roadmap, a governance baseline your counsel can sign, two build-vs-buy decisions made, and a board-update cadence. After that: up to five hours a week owning the AI agenda — vendor vetting, delivery oversight, hiring. Four seats total — when they’re full, they’re full.

Quarterly · Up to 5 hrs/week
Guarantee — Field Report onlyThree buildable AI features identified and the first one prototyped, or you don’t pay. hold us to this →
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 →
Mike Ulin
Founder & CEO

Mike Ulin.

Three-time AI founder. Built the first carrier-approved AI wildfire model at ZestyAI, the first generative-AI legal citator as CTO of Paxton, and the first remote solar-assessment AI at PowerScout. Four patents. Started at McKinsey; models he helped build now underwrite $4T+ in assets.

linkedin.com/in/michaelulin →
Founder’s work covered by
wsjreutersaxiosincnvidiageekwirelawcomlaw360abajournalinsurancejournalwsjreutersaxiosincnvidiageekwirelawcomlaw360abajournalinsurancejournal
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.

How is this different from hiring a consultant?

We’ve shipped the things we recommend — four industry-first AI products, two patents, models regulators approved. Advice comes from building, not from frameworks. And there’s no deliverable padding: the output is decisions, prototypes, and a roadmap, not a deck.

What does it cost?

The strategy session is free. The Field Report is $12,500, fixed. The fractional CAIO seat starts at $9,500/month for up to five hours a week, on quarterly terms. Prices are on the page because we don’t enjoy pricing theater any more than you do.

How much of your time do we get?

Up to five hours a week — recurring working sessions, async access, board meetings, and the standing right to ask “should we build this?” at 9pm. Four seats exist in total, so the attention is real.

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 ongoing management of outside build teams is part of the seat. We write the specs, review the work, and referee the estimates, so “two more sprints” stops being a lifestyle.