The Last 20%
Essays for the operational 20%
Short, opinionated essays on what stalls between 80% and production. For CIOs, CTOs, and CFOs at $50M-$1B engineering-led companies.
Subscribe on Substack- Essay 01
The Last 20%
Why Every Mid-Market AI Initiative Stalls at the Same Place
An engineering-led IT team ships an AI initiative at 80% within 90 days. The remaining 20% never closes — not because the team is lazy, but because the 20% is structurally different from the 80%, and almost nobody plans for the gap.
Read on Substack → - Essay 02
BYOK Is the Tell
A 30-Second Vendor Sorting Hat
One 30-second question separates AI vendors who'll be around in 2027 from the ones who won't. Ask it on every bake-off call — and watch the room reorganize itself.
Read on Substack → - Essay 03
Stop Hiring Platform Engineers
Hire One Less
The math on hiring a $200K platform engineer to maintain your AI stack vs. paying a specialist $50K/yr doesn't survive contact with a CFO who can do four-year arithmetic.
Read on Substack → - Essay 04
Pricing Transparency
$75K + $50K/yr — Here's the Build-vs-Buy Math
Most AI vendors hide pricing behind "talk to sales." Here's exactly what we charge — $75K engagement + $50K/yr — and why publishing the build-vs-buy math is the most defensible move we could make.
Read on Substack → - Essay 05
Year 2-3 of the PE Hold
When "We Built It Ourselves" Stops Being a Brag
There's a window in the PE hold cycle when "we built it ourselves" stops being a brag and starts being a liability. Recognize the window before the operating partner does.
Read on Substack → - Essay 06
The Power Automate Endgame Problem
Five Cliffs Every Mid-Market Deployment Eventually Hits
Every mid-market Power Automate deployment eventually hits the same five cliffs. The community knows about three of them. The other two only show up at scale.
Read on Substack → - Essay 07
What Cyber Insurance Carriers Actually Look at
In an AI Breach Claim
Five artifacts insurance carriers demand when an AI mediates a denied claim. Four of them don't exist in your current pipeline. Here's what they look like and where they go.
Read on Substack → - Essay 08
What I'd Tell a $50M–$1B CIO
If I Wasn't Selling Anything
Twenty minutes of unvarnished advice with no pitch, no demo, no NDA. Most of it is what to stop doing.
Read on Substack → - Essay 09
Cognitive Surrender
What Happens When Knowledge Workers Stop Reasoning and Dispatch Problems to AI Instead
A devops engineer named the failure mode of AI without discipline this year. Cognitive surrender is the decision to stop reasoning and let the model decide instead. Seven flavours of vendor-trust collapse, four cautionary cases at four scales, and the structural fix that is not "more AI literacy."
Read on Substack → - Essay 10
Seven Questions Every AI Vendor Should Be Able to Answer
A Buyer's Diagnostic for AI Vendor Evaluation
Seven questions you can run in a discovery call, RFP, or 30-minute vendor-eval review. One per vendor-trust-collapse flavour, with vendor-honest and vendor-evasion answer shapes laid out so you can tell which one you are hearing.
Read on Substack → - Essay 11
Two Kinds of AI Exclusion
And the One Your CGL Renewal Won't Tell You About
Headlines about carriers "excluding AI" blur two structurally different exclusions filed with state regulators. One is narrow and applies only to generative AI. The other is broad enough to exclude algorithmic credit scoring. Your renewal preparation needs to know the difference.
Read on Substack → - Essay 12
What You're Actually Deferring When You Defer Agent 365
Gartner Is Right to Say Wait. The Question Is What Fills the Deferral Window.
Gartner's First Take on Microsoft 365 E7 and Agent 365 says defer, and Gartner is right. The harder question is what you buy instead, and what you commit to operating yourself for the 6 to 18 months of the deferral window. The three honest paths, laid out.
Read on Substack → - Essay 13
The Ungoverned Marketing Department
Why Marketing Surrendered to AI First, and the Category That Is Still Empty
Marketing ships in public and the feedback is fast, so cognitive surrender showed up there before anywhere else. The marketing-operator cut of the Cognitive Surrender arc: what the failure mode looks like inside the department, and the governance shape that fixes it.
Read on Substack → - Essay 14
Integration Is the Moat
Portfolio Value Creation When Acquisition Velocity Stops Working
The cheap-debt, buy-the-growth roll-up playbook is closing. When you cannot buy the next turn of growth, the only return left is the one you build inside the businesses you already own. Integration is an operating capability, not a transaction.
Read on Substack → - Essay 15
The Job Description Is the SOW
The Open Marketing Requisition Is a Statement of Work With a Cleared Budget
Every portfolio company has a marketing requisition that has been open 60 to 120 days. The responsibilities section is a Statement of Work, the salary band is a pre-approved budget envelope, and the hiring manager is the named sponsor. The trial starts Monday.
Read on Substack → - Essay 16
The Vendors Just Named Our Category
Five Billion Dollars in Two Weeks, and the Segment the FDE Model Cannot Reach
In one fortnight of May 2026 the frontier vendors put more than $5B behind the Forward Deployed Engineer delivery shape, and stated publicly which buyers it will not reach. The partner-network half of that admission is the empty square the Operations Partner fills.
Read on Substack → - Essay 17
The Forward Deployed Engineer Will Not Be Coming to Your Office
Three Structural Responses for the $50M-$1B IT Organisation
The May 2026 FDE capital says who gets the embedded engineer: Fortune-500 regulated verticals. Mid-market IT is routed to partner networks and self-serve APIs. Three structural responses, decidable from engineering bench, time-to-production, and audit-artifact readiness.
Read on Substack →
New essays + audio podcast version, weekly
Subscribe to get each essay in your inbox + on the podcast feed.