Let's talk

Reliability is a design decision, not a model upgrade.

RAG pipelines, agents, and the evals that keep them honest. Consultant's questions, builder's answers, and an unreasonable interest in how things break.

Watercolour portrait of Landon Gray

they told me you couldn't build AI products in Ruby. they were wrong.

RailsConf Madison Ruby Blue Ridge Ruby Ruby Warsaw Boulder Ruby Flower City AI Changelog & Friends freeCodeCamp Indie Rails

What I'm actually good at

(and what I'll happily argue about)
01 · Retrieval

Context, on purpose

Chunking, ranking, and the unglamorous plumbing that decides whether the answer is any good.

02 · Agents

Loops with brakes

Autonomy is a dial, not a switch. Tool design, handoffs, and knowing exactly where the human belongs.

03 · Evals

Proof, not vibes

Graders and regression suites for work with no single right answer. This is the part people skip.

The notes

latest 5
All 15 notes
Alan Weiss and Knowing Your Worth raise your rates. today. Personal 2026.04.30 A Non-Engineer's Guide to Building Autonomous AI Agents with Claude Cowork my mom read this one AI 2026.03.15 Dario Took a Stand worth saying out loud Personal 2026.03.01 The Erosion of Corporate Sovereignty in the Midst of an AI Gold Rush on Substack · spicy AI 2026.01.28 external link Follow Your Curiosity — My Unexpected Path Into AI Engineering the origin story Career 2026.01.25 external link
unfinished notes stay up on purpose — that's where the thinking is. Browse the archive

Out loud

stages, mics, hallway tracks, and a couple of things I wrote
Landon alone on a theatre stage at Madison Ruby, standing on a green astroturf rug among potted plants, a slide behind him visualising a novel's word count
A conference room so full that people are sitting on the floor, Landon speaking at the front

barefoot on the astroturf at Madison Ruby, telling a room full of Rubyists that RAG belongs in Ruby.

Podcast · freeCodeCamp #213 What happens when the model can't fix it? 2026 · Remote
Podcast · Changelog & Friends An aberrant generation of programmers 2024 · Remote Podcast · Indie Rails #41 AI Consulting with Landon Gray 2024 · Remote
Every talk and appearance

Things I've built

shipped, in progress, and gloriously abandoned
over 100 side projects and counting — these are the ones worth showing. All projects
What it's like to work together
“A rare combination of technical expertise and leadership ability — he took the time to explain new ideas clearly, no matter how complex.”
Jenny Chervenkova AI Strategist, Dynamic Language on building an AI evaluation product together

Ways we could work together

a handful at a time, so each one gets real attention

I take on a small number of advisory, coaching, and speaking engagements. Staying close to other teams' problems keeps me sharp, and keeping the number small means the ones I say yes to get everything I've got.

Advisory

Sit in on the hard part

A standing hour or two while your team designs, debugs, or de-risks an agentic system. Flexible on timing.

Training & coaching

Evals your team keeps

A workshop on your own codebase, or 1:1 coaching for engineers moving into AI work. You leave with a harness, not a slide deck.

Speaking

Whimsical, thoughtful, informative

Keynotes, conference talks, and podcasts on agents, retrieval, evals, and doing AI work in Ruby.

How working together actually goes
Got a system that misbehaves?

Email first with what you're working on and the timeline. I'll tell you honestly whether I have room — and if I don't, who else to ask.

[email protected]