Coming from a military family, it was clear to Paul Madera in the 8th grade that he wanted to become an Air Force pilot — he has flying high ever since. In the world of venture capital, Madera is the quintessential outsider and Meritech Capital of which he is a co-founder must be the leanest firm in Silicon Valley despite its multi-billion dollar book. Till recently it had only six partners and it just hired its first non-partner. When Madera entered the business in 1999, it was a great time to raise money but a terrible time to invest as the events unfolding in 2000 would prove. Madera has put the learning to good use and has made many successful investments, the most famous being that in Salesforce and Facebook. He is still a big believer in Facebook and holds it in his personal portfolio. The sage-like Madera is a regular on the Forbes Midas List but has deliberately stayed low profile in his quest to find great late-stage investments.