Dev Interrupted The Odyssey of Innovation: Classics, Code, and Cognitive Load | Two Sigma's Matt Greenwood
May 27, 2025
Matt Greenwood, Chief Innovation Officer at Two Sigma, shares his insights drawn from over two decades in financial technology and a rich background in classical languages. He explores how ancient texts influence modern innovation and leadership. The conversation dives into the importance of adaptability, empathy in engineering leadership, and fostering a culture of curiosity. Greenwood also discusses utilizing AI to augment creativity, the significance of flexible goal-setting, and learning from past decisions to build resilient tech and teams ready for the future.
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Early Data Struggles at Two Sigma
- Matt Greenwood shared how early days at Two Sigma involved building data infrastructure from scratch without modern cloud tools.
- He personally cold-called vendors to access data and managed physical hardware before big data was common.
Innovation as Stacked S-Curves
- Innovation follows stacked S-curves where each plateau reveals new, unforeseen problems.
- Platforms enable seeing further but also demand fresh solutions continuously, not just faster fixes.
Epsilon Steps Toward Omega Goal
- Set a clear aspirational goal (omega) while taking deliberate small steps (epsilons) that advance it.
- Be forgiving of past architectural decisions and focus on evolving towards a better future.
