I've been in AI since 1998

I've been in AI since 1998. Back then, we called it T9 predictive text. I learned which numbers produced which letters. I got fast at it. Really fast. Oh, and learning what number combination from pagers meant: "143", "411", and "07734". Beep…

Stop It: Notes From Nearly 20 Years of Engineering Leadership

Stop scheduling "quick syncs" at 4:45pm to see who's still at their desk. Stop measuring productivity by commits or by butts in seats. Stop calling surveillance "collaboration culture." Stop running standups where everyone recites what they already said in Slack. Stop designing process…

The Day 300 Firefighters Watched My Architecture Burn

In 2012, at EVALS, I had a major problem on day one of our launch. "The wheels are falling of the go-cart!!" We were on site at a major fire academy. 300 users on 300 iPads, recording videos, photos, and notes in real time. All of it flowing…

YAML Files Longer Than the Code They Deploy

You don't know what sudo is anymore. You're shipping production three abstraction layers deep thinking the cloud is a place. It's not a place. It's a building in Virginia that smells like burnt dust and has a bizarre buzzing noise that nobody…

AI: Now Your Systems Can Fail at Scale!!! 🎉

If your software infrastructure and architecture needs AI to "produce incredible output," you've already lost. You're clearly coping for not knowing how to build systems that are maintainable, scalable, or reliable. Therefore....... AI. CANT. FIX. YOUR. BAD. FOUNDATIONS. It will just make them fail…

From Prompt Engineer to Crayon Evangelist: A 48-Hour Journey

What if the next hype is eating crayons? LinkedIn Titles/Tags in 48 hours: 🖍️CRAYON-NATIVE ARCHITECT 🖍️CRAYON EATING EVANGELIST 🖍️STRATEGIC CRAYON CONSUMPTION ADVISOR "Most people are eating crayons wrong. Here's my 7-step framework." "Just mass-recruited 400 people who've been eating crayons since 2019.…

We Planned Surgery And Built A Hospital Instead

The long story of combining two companies through an acquisition, from a technical perspective, in a little over 5 months. TLDR 2 completely different companies (GETOUTPASS and POGOPASS), were combined into 1 (GETOUT). We sunset 2 legacy platforms, migrated over 350k+ active members (representing over 1M active family pass holders)…

AI Certifications Are Bullshit

AI Certifications are the new fraud. I got one to prove it.I got certified in pencil sharpening last week. Twelve modules. Forty hours. There was a capstone project. I sharpened a pencil. It was a #2 pencil because, yah. I’m now a Certified Pencil Sharpening Professional (CPSP). Felt…

GraphQL Sucks

There, I said it. I've used GraphQL exactly once, and I had inherited it. Someone else's architectural confession left in the codebase like a note that just said "sorry." Never again. "But Jake, you must have had a bad experience with it, or…