Issue 02 — out now
Two AI companies in three years — one graduated, one in build. I teach companies how to use and deploy AI. Writing The AI Pragmatist for the executives navigating AI in real time.
Section 01·The Publication
Each issue: what shipped, what it means, what to do Monday. Written for non-technical leaders who need signal without jargon.
Section 02·The Work
UniWise · ContraSight
AI for clinical administrative spend. Three pivots in twenty-three months, $450K raised across angel and F&F, first place at UC San Diego Demo Day 2025, converted to Public Benefit Corporation. Wound down operations January 2026.
“First place at UC San Diego Demo Day 2025 — the celebration of a decade of student innovation at The Basement.”— UC San Diego Today
$0K
Raised
1st
Demo Day 2025
PBC
Converted Q3 2025
0
Months run
Pivot log
v1
2024
Calendar AI for students
Founding thesis. Built, shipped, learned the market wasn't there.
v2
Mid-2024
Operations copilot for SMBs
Pivoted toward paying buyers. Friction inside the buyer's stack killed velocity.
v3
2025
Clinical administrative spend
Final form. Demo Day winner. PBC conversion. Strategic wind-down January 2026.
Mauralink · Compatibility Engine
Better People Data.Better People Decisions.
Your process measures everything about the candidate. Nothing about the relationship with their manager. Mauralink measures the one thing that determines whether a hire actually works.
Grounded in 367 peer-reviewed papers of industrial-organizational psychology research. A graph of 33,000 entities. Eight validated compatibility dimensions. In design partnership with early customers.
0
Papers indexed
0
Entities in graph
0
Dimensions validated
Active
Design partners
Eight compatibility dimensions
Conscientiousness
How disciplined and reliable they show up.
Communication cadence
How often and how directly they exchange information.
Decision style
How quickly they commit and how they handle reversal.
Conflict tolerance
How they engage when stakes get tense.
Autonomy preference
How much oversight they need to do their best work.
Feedback orientation
How they give, receive, and act on critique.
Pace of change
How fast they accept and drive new direction.
Risk posture
How they weigh upside against unknowns.
Side ship · Open source · 2025
A directory of llms.txt files in the wild — the emerging standard for sites telling LLMs how to read them. Built in a weekend.
The Tools
I redact a lot of documents. I want my own AI workflows over real client data without leaking PII. So I built the tool, and I built the desktop client to live next to it. The portal at esfandiari.dev is where they live.
Halfshade · Document redaction · Subscription
halfshade.
Strip identity from documents. Keep the substance. PDF, DOCX, XLSX, CSV in; redacted markdown out.
Section 03·The Teaching
Workshops and embedded engagements with leadership teams that need to move on AI this quarter — not next year. The same lens I write under in The AI Pragmatist, in the room with you and against your roadmap.
Workshops
Strategy with leadership teams
Embedded
Deployment with your team
Section 04·Selected Essays
Section 05·What's Next
Rady MBA in progress. Panelist for UC San Diego's AI Council and Red Bull Basement Innovators. Building toward what's next — and looking for the people to build it with.
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