Last Wednesday, ReadWrite Editor-in-in-Chief Dan Lyons sat down with 27-year-old Box CEO Aaron Levie to discuss the complex market of enterprise cloud technology in the third ReadWrite Mix event in San Francisco.

(See also Box CEO Aaron Levie On The Uncertain Landscape Of Enterprise Software [Video])

In the one-hour sit-down, Lyons and Levie covered surprisingly diverse topics, from Levie’s personal life as a notorious workaholic to what it means to sit in the middle of the enterprise and consumer software landscape that has steadily begun to merge. Levie also showcased his sense of humor with descriptions of the companies he started as a teenager (Zazap, the fastest search engine on the Internet – except for Google), and spot-on caricatures of stuffy enterprise types to illustrate how he keeps his company loose and fast-moving. 

This 2:28 video touches on Levie’s thoughts on having grown up in the startup landscape with his high school friends, the laughable stereotype of enterprise software culture and seeking out mentors in Silicon Valley (Hint: There’s no risk to to sending an email. So what if you don’t get a response, he says).