Published via T: 2014-02-01 16:28:26

The year after he invested, Cuban and Levie disagreed about the ideal course for Box. Concerned about the threat of Google’s rumored GDrive competitor, Levie wanted Box to pursue a freemium land-grab strategy. He felt that it would be the quickest way to claim additional market share, even though it would definitely require raising tons more venture capital. Cuban preferred a more conservative approach of monetizing every user. Unable to agree, the man who many consider to be a ruthless investor politely bowed out, selling his shares at cost to Draper Fisher Jurvetson in Box’s 2006 Series A round.

My Two Cents

Even the "great" Mark Cuban doesn't get it right all the time. In this case, he was the first money into Box, which is now getting ready to go public. This is a really interesting case from the perspective of -- Cuban got this perfectly right as the first investor, but then a year later sold his shares to DFJ "at cost" b/c of a disagreement with CEO Levie. So he got it right, but got it wrong! Nobody's perfect.