https://news.ycombinator.com/item?id=450702, https://news.ycombinator.com/item?id=4060887
Also my personal list of favorites that entrepreneurs should watch (although not necessarily about technology):
Glengarry Glen Ross - http://www.imdb.com/title/tt0104348/
Moneyball - http://www.imdb.com/title/tt1210166/
The Pursuit of Happyness - http://www.imdb.com/title/tt0454921/
Jerry Maguire - http://www.imdb.com/title/tt0116695/
Catch Me If You Can - http://www.imdb.com/title/tt0264464/