Sarah Guo's Wager

Dom Cooke profiles Sarah Guo, who became the youngest general partner in Greylock's history at 28 and quit four years later to launch Conviction, a venture firm staked entirely on AI before ChatGPT shipped. The record since reads like vindication: pre-ChatGPT seed checks into Baseten and Harvey, each now worth over $11 billion, and first-year checks into Sierra, Cognition, and Mistral, together worth $54 billion. The wager of the title is the interesting part: the investor closest to the AI frontier is betting against the ambitions of its biggest companies, on the belief that the frontier labs will not capture every downstream product and market. The piece opens with a vivid account of the November 2025 agentic turn and runs eleven thousand words deep into how conviction, in both senses, gets priced.