Check out these threads:

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/

Not a movie, but Masters of Doom is a great book about the rise of ID Software (http://www.amazon.com/Masters-Doom-Created-Transformed-Cultu...)

This has a nice list. http://ventureburn.com/2013/11/5-great-movies-entrepreneurs-...

Code Rush. Documentary about Netscape: http://en.m.wikipedia.org/wiki/Code_Rush

E-dreams. about kozmo.com: http://www.imdb.com/title/tt0262021/

Startup.com http://www.imdb.com/title/tt0256408/

I strongly recommend watching Pursuit of Happyness - specially since it's based on a true story.

Also there is a series called BETA

- The social network

- The startup kids

- Jobs

- How America Was Built - (Rockefeller & Mellon)

- The CIA Movie With Colin Farrell.