A CTO's field notes
AI changed my job overnight.
I'm writing it all down.
I'm Keith Eddleman — 30 years in enterprise tech, currently neck-deep in what happens when AI stops being a buzzword and starts being your entire operating model. Every week I share what's actually working, what's failing, and what it feels like to make decisions this big with no playbook. Because there isn't one. So I'm writing it.
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“The master in the art of living draws no distinction between his work and his play. He simply pursues his vision of excellence through whatever he is doing and leaves it up to others to decide whether he is working or playing. To himself, he's always doing both.”
— L.P. Jacks
About the Author
Keith Eddleman
Enterprise CTO · Builder · Austin, TX
I've been building enterprise technology since 1995. CTO at Q1Media since 2012 — 135 people, $300M+ in media spend through a platform I built from scratch. I've taken more proof of concepts from napkin to production than I can count, and killed just as many that deserved killing.
Outside of Q1Media, I'm always building. AI platforms, autonomous agents, side projects that start as curiosity and sometimes turn into real products. I built an outbound revenue engine that runs without a UI. I built a fishing spot marketplace because I noticed my photos had GPS coordinates in them. I write this newsletter the same way I build — ship it, see what happens, iterate. You can see everything on the Projects page.
I'm not writing from a research lab or an analyst desk. I'm writing from the same chair you're sitting in — trying to move fast, make good calls, and not lose what matters in the process.
The kind of person who texts his son about code at midnight and considers that a good Tuesday.
What You Get Every Week
Proof of Concept to Production
I take AI ideas from napkin sketch to working system and document every decision along the way. Architecture, tooling, cost, tradeoffs — the full picture.
Practical AI for Enterprise
Not toy demos. Real applications in real companies — agent automation, infrastructure decisions, and the integration patterns that actually survive production.
What It Actually Feels Like
Most AI content tells you what to do. Almost none of it talks about what it's like to be the person deciding. The pressure, the trade-offs, and the moments where the right call isn't obvious. That part doesn't get written about enough.
Past Issues
Issue #12 · Apr 9, 2026
Death by a Thousand Subscriptions: The AI Containment Problem
78% of employees are bringing their own AI tools to work. Your controller just flagged 75 charges. Here's how to contain the chaos without killing the energy.
Read Issue →Issue #11 · Apr 6, 2026
Who "Owns" AI Inside Your Company?
Copilot is the participation trophy of enterprise AI. 3% adoption after two years. Here's who should actually own AI adoption — and the 6 models every company is fumbling through.
Read Issue →Issue #10 · Apr 4, 2026
The Workflow Revolution: When AI Forces You to Throw Out 20 Years of Dev Practices
Real talk on how AI coding isn't just changing what we build—it's forcing teams to completely re-engineer GitHub workflows, deployment cadence, and everything we thought we knew about shipping software.
Read Issue →Issue #9 · Mar 28, 2026
Website. Phone. Email. AI.
Zuckerberg says every business will have an AI — just like they have a website, a phone number, and an email. He's not predicting the future. He's describing the present.
Read Issue →Issue #8 · Mar 25, 2026
74 Releases in 52 Days. How Is Any CTO Supposed to Keep Up?
Anthropic shipped 74 Claude releases in 52 days. Meanwhile, 89% of enterprises are 'learning as we go' and 74% of CIOs regret a vendor decision. Here's a framework for operating in permanent uncertainty.
Read Issue →Issue #7 · Mar 23, 2026
B2A: Your Next Million Users Won't Have Faces
Y Combinator says 'make something agents want.' AgentMail, Moltbook, and Essentialist.io are already doing it. Welcome to Business-to-Agent — the category that kills per-seat pricing.
Read Issue →Why Listen to Me?
I don't have a podcast studio or a blue checkmark. I have production deployments, broken builds, and a terminal that's open right now. Here's what I bring:
Written for:
Got a war story? I want to hear it.
If you're building with AI and have a story worth telling — a proof of concept that became production, a migration that went sideways, a tool that changed your workflow — I want to feature it. No ghostwriting. No sponsored takes. Your name, your experience, your words.
You made it this far. That tells me something about you.
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