Ben Horowitz

Loudcloud went public in 2001 into a collapsing market, and Ben Horowitz spent the following years selling off its hosting business, renaming what was left Opsware, and steering that to a $1.6 billion sale to Hewlett-Packard in 2007. The Hard Thing About Hard Things (2014) is what he took from that stretch, written for founders and aimed squarely at the parts of the job with no good answer: demoting a loyal friend, cutting staff, telling people the truth when the news is bad. He and Marc Andreessen, his old Netscape colleague, founded the venture firm Andreessen Horowitz in 2009.