Andy Rubin (Android): "That's the way Google works, don't ask for permission for an idea, just go and do it. And then, when you are way beyond the point of no return, you're like, 'I need $200 million'"
Wesley Chan (Google Toolbar, Google Analytics): After Larry Page told him the Toolbar/Popup blocker was the "dumbest thing I've ever heard", Chan, a 'lowly' Associate Product Manager at the time, surreptitiously installed it on Page's computer and waited for him to mention how much faster his browser was running.
Paul Buchheit (Gmail, Later Friendfeed, Facebook, YC): IIRC he was the one who pushed for putting ads in Gmail based on the content of emails. When Google deployed this, it generated significant controversy and almost everyone considered it 'naughty' to say the least. Today, Gmail is the only place other than a search engine where I (and likely many others) click on any ads. The ads were important because providing Gigabytes of storage to millions of users for free is not scalable without generating revenue.
Google even tried to formalize naughtiness by making 20% projects, usually done as naughty skunkworks projects, part of the rules.
I actually have read those. I admit, part of my reaction was purely personal. I want to found a company so much it hurts. I'm smart, resourceful, creative, and determined. But I wouldn't say I'm used to getting my way, and breaking rules -- even in service of a higher goal -- makes me very nervous. (Think Hermione Granger.) So reading this was like getting hit in the gut. Not that it will stop me, but it highlighted how important the emotional aspects to founderhood are and how far I still have to go.
I've seen this trap with a lot of people who did well in school. For 12 formative years you're rewarded for performing tasks to spec and following rules, and you grow up and find that the things you really want to do involve transcending all the traits that got you where you are. That's the element of Google I'm referring to, I suppose. They make almost a cult of academic success, and for some people that was a kind of shining hope. And you, frankly, fit right into that. So to hear you say that guts might matter more in the end than brains hurts, even though I know you're right.