;Nupedia and the origins of Wikipedia 
 *"had struggled" had not necessary. It is generally more encyclopedic to write all past events in the simple past tense. Past perfect sort of has a grammatical purpose here to show that his struggles came before another past event, but since this is a chronological biographical article all past events come before other past events except the last one. Just use past tense throughout. ///WP:CHICAGO/WP:FOUR)   
 *Similarly had encountered -> encountered and had engaged -> engaged. ///WP:CHICAGO/WP:FOUR)   
 *"In an October 2009 speech, Wales recollects attempting to write a Nupedia article on Nobel Prize-winning economist Robert C. Merton, but being too intimidated to submit his first draft to the prestigious finance professors who were to peer review it, even though he had published a paper on Option Pricing Theory and was comfortable with the subject matter." is grammatically awkward. Break it down. ///WP:CHICAGO/WP:FOUR)