Articles

AI Transformation & Data

Agentic Engineering: What It Actually Means

Most companies saying "agentic" have a prompt template calling an API. Real agentic engineering is agents that create, QC, and compete with other agents.

Context Engineering: The 95% Nobody Talks About

Context is the 95%. The prompt is the last 5%. Why the retrieval, assembly, and layering pipeline determines AI output quality.

The AI Readiness Scorecard That Most Companies Fail

A pre-qualification scorecard for AI transformation engagements that measures willingness to change, not technical readiness.

The Case for Three People and Ninety Days

Why a 3-person embedded pod outperforms a 12-person consulting team for AI transformation — and the 30/30/30 methodology that makes it work.

Enterprise AI: The Organizational Willingness Gap

Why the gap between AI demo and AI production isn't a technology problem -- it's an organizational willingness problem that most companies refuse to confront.

Systems Thinkers Are the Superpower

Systems thinkers with business background are the highest-leverage people in AI -- and the disadvantage they faced in narrative institutions is now their edge.

Real Estate & Mortgage

One Pipeline Pretending to Be Ten Businesses

The mortgage industry is cost-plus. Every intermediary doubles the margin. One pipeline treated as ten businesses costs homeowners $90 billion a year.

The Mortgage Value Chain, Part 1: Who Gets Paid and Why

Real estate agents, the MLS, the $31 billion data infrastructure tax, and the 6% commission structure that costs American homeowners $97 billion a year.

Mortgage Value Chain, Part 2: The Hidden Rate Tax

How mortgage broker commissions and lender gain-on-sale get buried in your interest rate instead of appearing on your closing statement.

The Mortgage Value Chain, Part 3: Servicing Is Just Billing

In any other industry, this would be called billing. Mortgage invented a $200B industry by renaming billing and wrapping it in compliance jargon.

Title Insurance: A $20 Billion Tax on Bad Infrastructure

How a 5% loss ratio industry survives on regulatory capture and fragmented property records

The Proptech Pivot: Workflow to Data Company

The predictable pattern of proptech companies pivoting from workflow automation to data intelligence -- and how to spot it early.

Projects & Dabblings

What Changes When AI Remembers You

The gap between a stateless AI assistant and a persistent thinking partner changes how you make decisions, not just how you get answers.

Building a Personal RAG System in Three Iterations

18,000 chunks, sub-millisecond search, and three rewrites -- what building RAG over personal data teaches about retrieval at any scale.

Delaware Is a $40T Asset Manager Disguised as a State

The first state to operate like a SaaS platform already exists. It just doesn't know it yet.

Retros & Musings

The Cost-Plus Industry: A Mortgage Retrospective

Two million people make their living off the inefficiency. We just didn't think change was possible.

Being a Software CEO

Operating notes from six years as a software CEO -- people, architecture, customers, and the sequencing discipline that encodes founder judgment.

Why Decentralized Protocols Beat Startups

Why decentralized protocols solve problems that neither startups nor corporations can -- and why the advantage compounds.

Why NVIDIA Won the AI Era (and a Sovereign Fund Didn't)

Three years inside a sovereign wealth fund during the GlobalFoundries acquisition, and what the semiconductor bet teaches about buying capability, not just raw AI, in the compute era.

Our Generation Has Bitcoin

Why the generational wealth formula shifted from leveraged assets to hard money -- and why buying Bitcoin is simple but culturally hard.