Mike Monteiro of Mule Design gave an impassioned (and profanity-laden) talk at Webstock 2013, in which he discusses the importance of speaking up when a project is about to head downhill. I think it's a must-watch for anyone in the design world, and probably people outside of it too.
If you like Mike's talk, be sure to also check out his book.
Maciej Cegłowski (MAH-tchay Seh-GLOW-ski), creator and developer of awesome bookmarking service Pinboard, gave a great talk at this year's XOXO Fest (of which there's also a transcript with slides, if watching videos isn't your thing).
As one might expect if they follow the @pinboard Twitter account, Maciej is a very funny and intelligent man, and his talk reflected both sides of his personality. I highly recommend watching it, along with all the other videos being put out by the XOXO Fest people.
Another thing many people seem not to know about Maciej is that he's also a very gifted writer and has run a personal blog called Idle Words for a long time, filled with wonderful stories about travel, food, and technology. I'd start by reading Argentina on Two Steaks a Day and A Morning in Iceland.