The archive · 27 issues published

The Accidental CTO Chronicles.

Real startup stories. Comic strips. Technical lessons. Battle-tested advice — filed issue by issue.

Pinned issue#027 5 min· 24 Oct 2027

The OS Wars

Me (Linux). A Corporate CTO (Windows). A back-and-forth screaming match about which operating system is superior. 'Windows runs enterprise!' 'Linux runs the internet!' Then the designer walks in with a Mac. And we both stop.

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27 issues

Issue #027

Tech Life 5 min· 24 Oct 2027

The OS Wars

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Issue #026

AI & Tech Culture 6 min· 18 Oct 2026

The 1 Percent

A client left because our quote was too high. A week later, he returned ecstatic. He'd built the entire SaaS app using AI. He did 99% of the work. He just needed us to finish the last 1% so it could go online. Here's 100 bucks. The problem? That 1% is the actual software.

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Issue #025

Codebase Horror Stories 7 min· 12 Oct 2026

The Database Column

I opened the database and found columns named 'field1', 'field2', 'temp', 'temp2', and 'new_temp_final'. Then I found 'pt_odr_numbr_id'. No normalization. Reports built with queries nested inside loops. The budget didn't cover the therapy. But I fixed it anyway.

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Issue #024

Client Horror Stories 6 min· 8 Oct 2026

The Night Badger NDA

A masked client. A secret identity. An NDA thicker than a phone book. And a command system that keeps timing out because someone put surveillance feeds, vehicle telemetry, and crime analytics in the same database. I work in consulting.

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Issue #023

Tech Life 5 min· 1 Oct 2026

The Column Name Debate

I'm deep in a discussion about database design. Back and forth. Point and counterpoint. The kind of debate that shapes the future of a product. Then I realize I'm not talking to a colleague. I'm arguing with Claude AI about what to name a database column.

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Issue #022

Client Horror Stories 6 min· 27 Sept 2026

The Forever Project

An enthusiastic client with huge numbers. A small payment for a prototype. A SaaS idea that was always 'almost there.' I handed him to a friend. A year later, my friend fired him. 20 years later, he's still building it. Still almost there.

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