Dan Bricklin invented the spreadsheet -- personal computing's first killer app -- built and lost the first PC software empire and somehow remains a nice guy filled with ideas.
Dan Drake and a roomful of friends put together $59,030 and started Autodesk with a bunch of bad ideas and one that panned-out -- AutoCAD. Sometimes one is enough.
Although Brewster Kahle started and sold companies for big bucks, his true love is capturing the whole Internet at the Internet Archive, which he founded and runs today.