Education and Early Career
Woolner earned two bachelor's degrees from the Massachusetts Institute of Technology: one in Mathematics with Computer Science, and one in Management from the MIT Sloan School of Management. He also earned a masters degree in Decision Analysis from Stanford University.
After graduating from MIT, Woolner worked in software development and system management (for Oracle) and several start-ups in Silicon Valley; and later in product management (for SAS). During this time he maintained his avocational interest in baseball statistics and analysis. As he has written,
But no matter how interesting the technology or how novel the application, it was hard to get truly passionate about helping another business improve their profitability or run more efficiently. The work was intellectually stimulating but not emotionally engaging.
What did engage me was baseball statistics. I spent a lot of my free time reading online forums devoted to baseball, and I discovered that baseball statistics had moved far beyond the stats on the backs of the baseball cards I grew up with. I started designing my own customized statistics in the mid-1990s and eventually posted them on Usenet newsgroups and my own Web page.
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