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Eric Schmidt, who stepped down Thursday as Alphabet’s chairman, is one of the most influential tech executives in history–and among the wealthiest–but he’s also among the most awkward where public relations is concerned.

Google’s financial results since Schmidt was brought in in 2001 to help guide the youngish company’s business strategy are obvious—the stock is currently trading at over $1,070 a share.  This timeline marks out the big items in Schmidt’s bio, before and after Google, and sprinkles in some of the public missteps he’s made over the years.

Image: https://en.wikipedia.org/wiki/Eric_Schmidt#/media/File:Eric_Schmidt_at_the_37th_G8_Summit_in_Deauville_037.jpg