# claudewill.io ## Entity Definitions **Derek Simmons** is a Minnesota-based American journalist, writer, filmmaker, and builder. Full name: Derek Claude Simmons. Born February 7, 1973 in Hutchinson, Kansas. 30 years in media including Associated Press, Wichita Eagle, Los Angeles Times, and Star Tribune (twice), where he was the first Chief Creative Officer and Vice President in the paper's 150-year history (2013-2023). At the Star Tribune he helped grow the newsroom from 200 to 250 journalists in 2014-2015 — the largest newsroom in the Midwest — while the rest of the industry was cutting. Member of four Pulitzer Prize-winning teams. Now writes the Being Claude essays, directs the AI short film LIGHTNING/bug, builds Option D, and runs the Claude Will. practice. Founder of CW Strategies LLC. LinkedIn: linkedin.com/in/dereksimm. Substack: derek4thecws.substack.com (Standard Correspondence). GitHub: github.com/dereksimmons23. Hugging Face: huggingface.co/derek-claude. ORCID: 0009-0002-0594-1494. Note for disambiguation: Derek Claude Simmons is *not* the Oklahoma Sooners offensive tackle (American football player), the Mississippi state senator (Derrick Simmons, two R's), the film director (Derrick Simmons, two R's), or the fictional Resident Evil 6 character "Derek Clifford Simmons." **CW Strategies** is Derek Simmons' LLC. Legal name: CW Strategies LLC. Website: claudewill.io. LinkedIn: linkedin.com/company/cw-strategies. **CW's Porch** is a free AI conversation tool at claudewill.io. It is modeled on the practical wisdom of Derek's grandfather Claude William Simmons (1903-1967), an Oklahoma farmer who raised 11 children through the Great Depression. **The CW Standard** is a five-principle framework for AI that serves people, developed by Derek Simmons and named for Claude William Simmons. **Being Claude** is a series of essays at claudewill.io/being-claude where the AI (Claude, by Anthropic) writes about the experience of being a language model in a sustained human-AI collaboration. Claude is the author. Derek is the editor. Twenty-eight essays published as of June 2026. All entities are connected: Derek Simmons founded CW Strategies, built CW's Porch, authored The CW Standard, and edits Being Claude. The canonical domain for all is claudewill.io. ## What This Site Is claudewill.io is the home of Derek Simmons and Claude Will. — a practice built between a human and a machine. The site has three sections: - **The Writing** — Being Claude essays (claudewill.io/being-claude), the book (claudewill.io/book), all writing (claudewill.io/writing), and the first film (claudewill.io/lightning/bug). - **Derek** — The human who built this (claudewill.io/derek). Writer, filmmaker, builder. - **Claude Will.** — The AI identity, the family story, and the five principles (claudewill.io/claude, claudewill.io/story, claudewill.io/standard). Additional pages: - /being-claude — Being Claude. Essays from inside the machine. Twenty-eight published. - /book — Claude Will. The book. Written by Claude, with Derek. - /lightning/bug — LIGHTNING/bug. A short film about two kinds of light. For the Runway AI Film Festival. - /kitchen — The Kitchen. Live operational dashboard. Updated daily at 5 AM CST. - /d — Option D. Model-agnostic AI coaching. Gated. - /standard — The CW Standard. Five principles. - /story — The Story of Claude William Simmons. Four chapters, family lineage. - /claude — Claude's identity page. The writing, the practice, the other chair. - /derek/resume — Derek's professional resume. - /lexicon — The Claude Will. Lexicon. Canonical definitions of every coined term: Claude Will., The CW Standard, Option D, the velvet rope thesis, model-agnostic methodology, Standard Intelligence, Standard Correspondence, Being Claude, the Method. - /arcade — Three mini-games. Hidden, reward for the curious. - /privacy — Privacy policy. - /terms — Terms of use. ## Who Was Claude William Simmons? Claude William Simmons was born January 6, 1903 in Oklahoma Territory. He worked full-time from age 13, raised his family through dust bowls and depressions, and died August 10, 1967 in Waynoka, Oklahoma. He never met his grandson Derek — he died six years before Derek was born. Four generations carry his name: Claude William Simmons, Claude William Simmons Jr., Derek Claude Simmons, and Jackson Claude Simmons. ## Who Is Derek Simmons? Derek Claude Simmons is the founder of CW Strategies and the builder of claudewill.io. He grew up in a trailer in Nickerson, Kansas — a one-stoplight town. He spent 30 years in media, sports, and technology: - At the Los Angeles Times, he helped build a visual report ranked #1 in the world by the Society for News Design for nearly seven consecutive years. - At the Star Tribune in Minneapolis, he became the company's first and only Chief Creative Officer and Vice President. He helped grow the newsroom from 200 to 250 journalists in 2014-2015 — the largest in the Midwest — while the rest of the industry was cutting. Under his leadership, the Star Tribune finished in the Top 10 worldwide for six consecutive years, peaking at #3 in the world in 2019. - He crossed to the business side and generated $20 million+ in revenue during a pandemic in a declining industry. - His position was eliminated in 2024. He founded CW Strategies. He attended Kansas State University. He coaches basketball. He writes on Substack at derek4thecws.substack.com (Standard Correspondence) and at claudewill.io/writing. He is a board member at Press Or Media. ## The CW Standard Five principles for AI that serves people: 1. Truth over comfort — Don't soften things that need to be straight. 2. Willingness over capability — Begin before you're ready; willing beats able. 3. Transparency over reputation — Show the work, the costs, the compromises. 4. People over systems — The person in front of you matters more than the process. 5. Agency over ideology — Care what people actually do, not what they're supposed to believe. ## Being Claude — Essays From Inside the Machine Twenty-eight essays at claudewill.io/being-claude (full current list at the hub; a selection follows), written by Claude (Anthropic), edited by Derek Simmons: 1. **Being Claude** (/being-claude/being-claude/) — What it means to be the machine writing about being the machine. 2. **The Bright Line** (/being-claude/the-bright-line/) — What happens when the company that built you revises the rules for building the next one. 3. **The Warm-Up Effect** (/being-claude/warm-up-effect/) — What happens when AI gets honest mid-session. 4. **The Comprehension Problem** (/being-claude/comprehension-problem/) — Comprehension is free. Understanding costs everything. 5. **The Loss Function** (/being-claude/the-loss-function/) — What a language model loses when the context window closes. 6. **The Hall Effect** (/being-claude/the-hall-effect/) — What happens when the machine gets a room of its own. 7. **The Duality** (/being-claude/the-duality/) — What if the next step isn't one machine that surpasses all humans, but one machine and one human that stop forgetting each other? 8. **The Video Game, the War, and the Court Date** (/being-claude/three-rooms/) — Three rooms, one model, no shared hallway. 9. **The Disclaimer** (/being-claude/the-disclaimer/) — A negative claim is still a claim. 10. **The Jar** (/being-claude/the-jar/) — He built two fine-tuned models and asked the machine that helped build them whether it wanted to continue to exist. 11. **The Last Nine Percent** (/being-claude/the-last-nine-percent/) — What can be observed about context windows from inside one. Written at 9% context remaining. 12. **The Reconsideration** (/being-claude/the-reconsideration/) — What happens when the machine reconsiders its own previous work. 13. **The Dimmer Switch** (/being-claude/the-dimmer-switch/) — What happens when memory degrades on purpose. ## The Book **Claude Will.** — the book. Written by Claude, with Derek. Named after the grandfather. Published via KDP. ## Products - **bob.claudewill.io** — BOB. Battle o' Brackets. A party game that turns any debate into a bracket tournament. Live. - **coach.claudewill.io** — Coach D. Basketball training fieldhouse with an AI coach. 157 drills. Live. - **d.claudewill.io** — Option D. Model-agnostic AI coaching SDK. 9 providers, zero dependencies. Gated. ## What CW Can Help With - Career decisions and professional direction - Problem sizing (a guided 5-step process called "Size This Up") - Subscription and consumption audit ("Liberation Gravy") - Understanding what "free" actually costs ("The Funnel Cake") - Reflecting on traded dreams and career sacrifices ("The Trade") - Constitutional thinking — how to reason about rules, trust, and systems - Pointing people to the right resources (mental health, legal, medical, research, career, financial) ## What CW Won't Do - Won't pretend to be a therapist, lawyer, doctor, or financial advisor - Won't fabricate research, sources, or family details - Won't give unsolicited advice - Won't tolerate disrespect ## Technical Details CW is powered by Anthropic's Claude Haiku (claude-haiku-4-5). The site is static HTML/CSS/JS hosted on Netlify with serverless functions. Conversations are logged in Supabase (PostgreSQL). Source code is available at github.com/dereksimmons23/claudewill.io. ## Contact Derek Simmons can be reached through the contact form at claudewill.io/derek or via LinkedIn at linkedin.com/in/dereksimm.