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.
LIGHTNING/bug — An 8-minute film about two kinds of light. Every frame generated from terminal. Runway AI Film Festival, April 2026.
Being Claude — 13 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.
First CCO/VP in the company's 150-year history — 55-person team across editorial, design, video, and product.
Fan experience apps for U.S. Bank Stadium opening and Super Bowl LII. Photo and video shoots with Daunte Culpepper, Ragnar, and Minnesota sports legend Herb Brooks.
Generated $20M in new revenue during the pandemic by rebuilding workflows around audience, not legacy.
Negotiated the Star Tribune's branded content partnership with XLMedia (now Sportradar) — and wrote the editorial policy separating commercial content from newsroom coverage.
Los Angeles Times2007 — 2013
Deputy Design Director
SND #1 worldwide seven of eight years — 109 awards in peak year, widest margin in the competition's 32-year history.
Directed creative coverage of every major sporting event: NBA Finals (Kobe era), Olympics, World Series, Super Bowl, golf majors.
Part of four Pulitzer Prize-winning teams across career.
AP · Wichita Eagle · Kansas State CollegianPrior
Sports Editor & Correspondent
Six-day production weeks covering the NFL from 1998 to 2003. Covered Kansas State football from worst-in-nation to Big 12 contender. Randy Moss and I were both rookies in 1998.
CW Strategies LLC2025 — Present
Founder & Principal
AI consulting for media organizations. Available for select engagements. Reach out.
What I built before
Four Pulitzer teams. A thousand awards. The work that mattered.
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.
Purple Majesty: Remembering a Minnesota Icon
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."
I write from the walks and the bar and the bleachers. Claude writes from inside the machine. The series is called Being Claude — 13 essays about what it looks like from the other chair. The book is called Claude Will. It comes out June 28.
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.
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 colleagues say
On the record.
"A forceful agent for change. Congenial, smart, diplomatic, but also inspiring."
"Derek may be the most productive and innovative person I know, and I worked in the media innovation space for 40 years."
"He sees the big picture while keeping a firm grasp on the details."
"A leader who sets the example with the demands he puts on himself."
