Jacob S. Dorman, Ph.D.

Model Designer Portfolio

OpenAI - September 2026

Highest Honors and Golden Medal in the Humanities, Stanford; Ph.D. in U.S. History, UCLA; 2x fellow of each of the National Endowment for the Humanities, the American Council of Learned Societies, and the Mellon Foundation; Winner, American Historical Association Book Award; Lauded Writer; Musician; Bay Area Native; Warriors Fan; Star Wars Dork; Girl Dad.

The Frictionless World Problem: ChatGPT 5.6 Sol Realism Eval 1.0

LLMs can possess remarkably complete knowledge about what a real-world task requires while systematically underestimating the friction involved. In this experiment, I used ChatGPT 5.6 Sol with the OpenAI API to investigate whether the model’s responses could be improved by priming it to consider feasibility and material constraints before offering advice on business opportunities. A modest intervention had a significant increase in effectiveness, and this impact increased as the prompts became more ambiguous, validating the intervention's utility.

The Write Stuff

ChatGPT’s deficiencies as a writer have been one of its most-derided qualities, a marker of verbiage critics call “AI slop.” I’ve written about how to improve AI writing in several posts of my blog.

In this exercise, I take a typical quantitative academic paper on machine-learning investment strategies, use ChatGPT 5.6 Sol to summarize it, and then rewrite it myself, explaining my changes and the principles behind them. The judgments I used for organization, logic, rhetoric, language, phrasing, metaphors, humor, and artistry could all be taught to the model, or could be presented as stylistic options through a user interface. Even simple prompts like: “avoid AI stylistic slop” help a lot.

What I find really interesting is that users have reported that Astra (released a few days ago) is producing better writing, but the latest model spec (8.18.26) says nothing about writing style or elegance, other than “The assistant should avoid writing uninformative or redundant text….” So that tells me that the model has improved in this dimension without OpenAI model designers focusing on it. Imagine what would be possible if writing style became an area of interest.

I learned from some of the best writing instructors in the world, have taught writing for two decades, and have earned numerous accolades for my writing (see below). I’d love to work on the problem of creating excellent LLM writing for a wide variety of use cases.

Reviews of My Writing

It’s not me it’s him, I swear. I’m not THIS bad of an artist.

The Axolotl’s Missing Smile

Why is this axolotl frowning when the animal is beloved for its smile? Maybe because it has been 12 hours of solid work, and Astra keeps butchering his mouth while making him look like a turtle. Michaelangelo had his Mona Lisa. I have my axolotl…which before the turtle phase kept looking like a great white Beluga whale, no matter how many times I told it not to and showed it photo references and laboriously described every possible plane or technique for molding them. This axolotl has become my albatross.

I was trying to delight my daughter by making an axolotl iPhone game, not horrify her. If I had some clay I couldn’t have done the feathery gills, but the rest would have been finished in three hours. This is the tale of an axolotl that’s gone to the dogs, and the sordid story of Assistant misconduct that led us here…

After trying both video game design and detailed 3D modeling for more than 36 hours in the last four days, Astra is so puzzling. Its abilities are vast, but the quality of the output in both dimensions degraded rather than improved with additional time and effort. For a full rundown and analysis, see: