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Trick is: Stay long enough in the game, earn enough money to stay afloat, then find the gold at the end of the rainbow. Expose yourself to luck.

Indeed. And he was very selective and disciplined about what he chose not to do.

Many gurus are bad businesspeople. (What makes them a good guru contradicts the nuts and bolts of running a company) I'm glad to see how well he's done.

Trello was what convinced me he'd really got it. It's got like 1% the features of Jira - and is 10x more useful because of it.

Dave Winer maybe?