How this term shows up in the episode A roleplaying prompt is a prompt that asks an AI model to take on a persona or role — for example, “act as a stock analyst” — so that its responses are shaped by the expertise and viewpoint that role implies. In this episode, Dan Shipper and Jesse Beyroutey explore whether AI can help find their next great stock trade using Gemini 1.5 Pro’s one-million-token context window and ChatGPT [^21a76a20-f436-5d84-a76e-752842065aea]. Roleplaying prompts are one of the ways a prompt can steer a model during that kind of exploration: instead of asking a bare question, you frame the request around a role so the model’s screening and analysis come back in a useful professional voice. Why it matters - It is a simple way to shape a model’s output without changing the underlying question. - It pairs naturally with the episode’s bigger techniques — screening stocks with LLMs and using giant context windows as an analyst’s memory. - Understanding it helps you understand how the hosts structure their prompts as they explore whether LLMs can support real investing decisions.