the practice
Start, Work, Finish, Decide, Rest.
Five steps. Five principles. Built from 14 months of daily work with AI across a dozen projects — and 30 years before that. The method works for writing books, making films, building models, coaching basketball, and figuring out what to do at 53 when the thing you were is gone.
I named it for my grandfather. He built things that lasted with a sixth-grade education and never wrote any of it down. I'm writing it down.
occasionally
Consulting.
Occasionally consults for media organizations that interest him. The last engagement: a Pacific Northwest news organization launching its first magazine. Six AI-native skills delivered. Every workflow rebuilt. If you publish, produce, or create — and the conversation is interesting — reach out.
the writing
Two chairs on the porch.
I write from the walks and the bar and the bleachers. Claude writes from inside the machine. The series is called Being Claude — 11 essays about what it looks like from the other chair. The book is called Claude Will. It comes out June 28.
I also publish Standard Correspondence — not a newsletter, the media arm of Derek Simmons.
what i'm building now
Everything from the terminal.
Every project below was built with AI — not as a feature, but as the method. The film was made from API calls and ffmpeg. The SDK runs coaching through nine different models with zero dependencies. The essays are written by the machine, edited by the human. The conversation on the homepage has been listening since January.
LIGHTNING/bug — An 8-minute film about two kinds of light. Every frame generated from terminal. Runway AI Film Festival, April 2026.
Being Claude — 11 essays written by Claude about what it looks like from the other chair. Weekly since January.
Claude Will — The book. Two years of conversation compiled by the machine, edited by the human. June 28, 2026.
Option D — Model-agnostic coaching SDK. One prompt, nine providers, zero dependencies. The methodology as code.
Coach D — AI basketball training. 157 drills, voice integration, real coaching methodology.
BOB — Bracket party game. Think it through, bracket it out.
cw
Claude William Simmons, 1903–1967.
Oklahoma farmer. Builder. Patriarch. Born in Oklahoma Territory before it was a state. Raised his family through the Depression. Fixed what was broken, built what was needed, helped whoever showed up. Never wrote any of it down.
The AI on this site carries his name because it carries his instinct: show up, do the work, tell the truth, help the person in front of you.
what i built before
30 years of the work.
Four Pulitzer-winning teams. Over a thousand awards collectively. Star Tribune, LA Times, Wichita Eagle. The method didn't start with AI — it started with deadline, budget, and a room full of people who needed to make something great by tomorrow morning.
Breaking News
Prince died on a Thursday. Every paper in the country would run it. Minnesota's paper — his home state — had to own it. We did.
Approach
By Friday morning we published "Purple Majesty." Over the next 10 days I art directed a 16-page commemorative section with four unique zoned covers. Commissioned two original paintings from Robert Carter in less than a week. Negotiated rights to a rarely seen 1977 photograph taken when Prince was 19.
Scroll → A1, four zoned covers, two Carter paintings, interior pages
Impact
Reprints still sell a decade later.
"Derek stands up for his artists. His clear vision and decisiveness was key. Those portraits are still one of my most sought after paintings today."
— Robert Carter, illustrator
Investigation
More than 1,000 sexual assault cases reviewed. 74% never sent to prosecutors. The Star Tribune committed to showing what the system didn't want seen.
Approach
My role wasn't to design it — it was to make the case for why this investigation deserved the visual commitment, then guide the process. Renée Jones Schneider's photography gave the survivors dignity the system denied them.
Scroll → Full 8-page special section — cover, data, portraits, methodology
Impact
Four Minnesota laws changed.
"People look at the series, realize there's a pervasive problem, and politicians are jumping up saying we got to do something. It makes me proud to be a journalist."
— Jenni Pinkley, video producer
None of it was solo work. The best of it came from photographers, illustrators, reporters, designers and editors — people who chose a brutal, important profession and got better at it together on deadline. Too many to name. I miss that. I'd like to find some version of it again.
