Grammarly

Grammarly captured the writing assistance market before AI language models could write coherently — the business model was subscription access to automated proofreading when the alternative was hiring human editors. Then OpenAI released ChatGPT and the entire value proposition inverted: users do not want tools that improve their writing, they want tools that do the writing. Grammarly added generative features in 2023 but the core product remains editing assistance while competitors offer end-to-end document generation. The company has 30 million users and $200M+ in ARR but growth has visibly slowed as free AI alternatives absorb the market Grammarly spent a decade building. The $13B valuation was set in 2021 during peak SaaS multiples — today it prices a subscription editing tool at the same level as companies building foundational AI infrastructure, which is either pricing in a product pivot not yet executed or pricing in a past that no longer exists.

VERDICT: HUNTED — Grammarly spent 13 years building a $200M subscription business that makes writing better, then OpenAI built a free tool that does the writing, and the distance between those two products is the distance between a $13B valuation and obsolescence