Arrived in Silicon Valley from Texas five years ago a “washed up corporate executive” who couldn’t land a partner gig on Sand Hill Road. Apprenticed at August Capital and Foundation Capital, before he started investing his own money: His first bet was on a now-defunct company called Odeo started by then-unknown entrepreneur Ev Williams. When the company folded, Williams tried to give Maples his money back. Maples told Williams to keep it for his next company. The result? A $25,000 uber-early investment in Twitter and major league return. A $500,000 check to textbook rental company Chegg may be worth even more. Investment strategy is to pursue “thunder lizards”--disruptive, swing-for-the-fence-type plays that everyone finds ridiculous. That has led to early investments in ngmoco (sold to DeNA for $400 million), SolarWinds (went public, current market cap: $1.6 billion), Digg, Gowalla, Kno and a dozen other successful startups. Got start cofounding Motive, one of the only successful technology IPOs of 2004. Until July 1995, Mr. Maples was Executive Vice President of the Worldwide Products Group and a member of the Office of the President of Microsoft Corporation. Mr. Maples, who joined Microsoft in 1988, has over 30 years of experience in the computer industry. Before joining Microsoft, he was Director of Software Strategy for IBM. Mr. Maples also serves as Chairman of the Board of Directors of Multimedia Games, Inc. and as a director of Motive, Inc. and Sonic Corp.