Flirting with Models Flirting with Models

Ben Wellington – Complex Feature Engineering at Two Sigma (S7E32)

Jul 6, 2026 · 56m

Summary

Corey Hofstein interviews Ben Wellington of 2Sigma on the critical role of feature generation in quantitative investing. They discuss how large language models are democratizing data creation, allowing researchers to rapidly prototype novel signals like CEO micro-expressions. The conversation highlights the tension between AI’s efficiency and the need for orthogonal, diverse alpha, warning that over-automation risks homogenizing strategies.

Topics discussed

Intro, Return Stacking Symposium, and podcast overview Ben's background: NLP, 2 Sigma, and feature generation Defining features: From price changes to news sentiment Pod shop vs. shared platform models at 2 Sigma Where alpha lives: Data, features, and forecasting Human priors, creativity, and avoiding noise in features Collinearity, orthogonality, and signal decay Hiring for ingenuity and lateral thinking skills LLMs as data generators and research accelerators Democratization of tools and the risk of convergence Timing technology adoption and infrastructure choices Model control, hallucinations, and preventing overfitting Data upgrades, diminishing returns, and knowing when to ship Scaling idiosyncratic insights and the changing role of coders AI as an amplifier and Ben's obsession with city data
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