25:09Buy Now, Maybe Pay Later: Dealing with Prompt-Tax While Staying at the Frontier
Andrew Thompson explains the “prompt tax”: the uncertainty and rework that can come with upgrading an AI product to newer models. Using Orbital’s real estate due diligence software as an example, he describes its growth, its reliance on domain experts and prompts, and its informal evaluation practices. He shares tactics for adapting prompts to reasoning models, migrating prompts with newer models, using feature flags, and acting quickly on user feedback. His central advice is to keep shipping at the AI frontier, manage risk through progressive rollout, and decide case by case whether the upgrade’s benefits justify its costs.