Jenny Xiao's path is unusual for a VC—she went from AI research at Columbia to working at OpenAI (which she first knew as a client of a small AI consulting firm she started in college) before moving into venture, and she still spends hours each day using tools like ChatGPT and Cursor while asking founders deeply technical questions about their model choices and GPU needs. She looks for founders who are extreme in one specific skill rather than well-rounded, avoids startups that are just thin layers on top of big AI models, and tests ideas by asking whether a company would still matter if AI models got 10-20% better or if OpenAI or Google could easily copy them—all while bringing a personal love of gaming and GPUs into how she thinks about technology.