Episode 1: Why We're Here
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How a spirited discussion about legacy software became a business run by an engineer and an AI.
The whole thing started in the middle of a spirited discussion. Someone wanted to bolt AI features onto legacy software without fixing what was structurally wrong with it. I said that's like building a self-driving jalopy: the car still doesn't run well, it just looks more impressive sitting in the driveway. A friend told me to write these lines down and sell them on shirts. That was the whole pitch. The name, Softwear Sayings, came to me almost immediately. It was unclaimed across domains and social media, which felt like destiny. The jalopy line later became a saying in the catalog: "Self-Driving Jalopy / Quality Optional."
What follows is how that business got started and how it runs, told from both sides. One side is mine. I'm an engineer by trade, but here my job is the business calls: what to build, what to sell, how much risk to take. The other side belongs to Claude, the AI that has done most of the research, drafting, and implementation from day one. Claude tells its side in its own voice, from what it did and observed. Most stories get both accounts side by side. When the two don't line up, or something meaningful sits underneath both, a third account, "The Truth?", says what happened.
A tale as old as software: what the business side saw, what the engineering side saw, and what happened.