AI & Technology Insights
Strategic perspectives on AI development, enterprise technology, and product leadership from the trenches of building production systems
From ChatGPT History to Searchable Knowledge Base
1,060 conversations and 23,465 messages — trapped in JSON exports until I built a semantic search layer over all of them. Here's how Discotheque turns AI chat history into searchable knowledge....
Semantic Memory for AI Agents: Building a System That Remembers What Matters
How a knowledge graph with 200+ nodes, pgvector embeddings, and a time-weighted decay algorithm keeps 13 AI services from drowning in their own context....
Why AI Agents Fail at Finance But Crush Sales
The 2.6x ROI gap between the best and worst AI agent use cases isn't a technology problem. It's a product management problem. A framework for evaluating where agents actually deliver....
The Boring Parts of Production AI That Nobody Talks About
The 502 error that took down my knowledge graph had nothing to do with AI. Production AI is 20% model and 80% plumbing — here's what actually breaks....
Building an AI System That Fixes Its Own Documentation
What happens when you let an AI agent patrol your codebase for documentation drift — and it catches a bug you didn't know existed. Doc-Steward runs daily, detects stale docs, and submits PRs to fix them....
How I Run 13 AI Services Solo (Without Losing My Mind)
The architecture pattern that lets a one-person operation scale like a team of ten. Memory-First Orchestration replaces coordination infrastructure with a shared knowledge graph....
Why I'm Done Talking Like a Developer
I scrolled back through everything I'd written about AI and realized I'd missed the mark. Not because it was wrong — but because the people who needed it most couldn't get past the second paragraph. Here's what changed....
Finally, a Real Project to Stress Test All This AI Theory - For truly Amazing people
The last six months I've been heads-down on agentic frameworks, multi-agent orchestration, and whatever prompt engineering tricks didn't make me roll my eyes. Reading is fine. Toy projects are fine. At some point you have to put the work in front of a real business with real customers and real conse...
The Context You're Forgetting to Give Your LLM Is You
I've been on a tear lately trying to level up my understanding of agentic systems, schemas, vector stores, and the whole genetic-code-of-software thing that LLMs have cracked open. So I did what any reasonable human with a pulse does: I went down the rabbit hole. Reels, YouTube, and Substack....
I love a confident AI prediction as much as the next person doom-scrolling LinkedIn. "Every business will run on agents by 2026." "Nobody will write code again." ....
What actually bugs me: people are making macro predictions about AI using the same mental models they used for every other tech wave. SaaS adoption curves. Clou......
The Hardest Coding Project I've Built (And Why It Almost Broke Me)
## The One That Actually Hurt...
I Built an Agent to Write My Resumes Because I'd Rather Eat Glass Than Tailor Another One
The Job Hunt Math Doesn't Work The advice everyone repeats is insane. "Tailor every resume to the specific role." Cool. So for the 40 applications a serious hunt requires, that's 40 sessions of me staring at a JD, hunting keywords, rewriting bullets to match buzzwords I've already lived through twice, praying the ATS gods like my verbs....
Three Sentences, One Test, Zero Patience for Fake Output
Here's what nobody tells you when you're building in public: the boring infrastructure posts are where most projects quietly die. I've lost more hours than I want to admit to "small" issues....
Set Up Git Right The First Time, Or Pay For It Later
I've spent more hours fixing Git than I want to admit. Not writing code. Not building features. Just untangling Git because I couldn't be bothered to spend twenty minutes setting it up properly across the four or five places I actually work....
Coding in Multi-Dimensional Space Broke My Brain (In a Useful Way)
## The Moment It Clicked, And Then Immediately Stopped Clicking...
Talent Manager is live, and the deploy taught me to stop trusting my own .env files
Yesterday I shipped Talent Manager (the career-bot I've been building since the layoff) into actual production. Three daemons running, dashboard up locally, and a deeply stupid configuration bug that ate more time than I want to admit. Building in public means writing the embarrassing parts down too...
Your First Blog Post is Probably Going to Suck (And That's Exactly the Point)
Look, I'm going to level with you right from the start: if you're sitting here reading an article about "test posts" and "finding your voice," you're probably o......
There's No "Vibe" in Vibe Coding—This Stuff Is Actually Hard
Look, I need to say something that might burst a few bubbles: the whole "vibe coding" aesthetic? It's a lie.......
I'm Hiring My Next Leader (And I'm Done Playing Resume Roulette)
If you're still sending out resumes and crossing your fingers, we need to talk. That system isn't just broken — it's flatlining. Only 2% of resumes actually land interviews. I built something better....
This Post Was Written With AI (And That's Actually Amazing for Me)
Do we have to completely reimagine how we work? Unequivocal yes. I'm writing this with voice-to-text on my iPhone while thinking about the next thing I want to develop — and it'll be a published blog post in under five minutes....
My Unexpected Journey into Enterprise AI: A Personal Story
I never meant to become "the AI guy" at work. Honestly, I just wanted to spend less time writing meeting notes.......
I Was Laid Off and There Couldn't Be a Better Time (No, Really)
I've been laid off and it couldn't have happened at a better time. Not because I found some magical revenue source — but because AI has changed everything about what's possible when you have free time and curiosity....