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 →
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