linux.conf.au has a charity auction over dinner. There are various failure modes:
There’s always been a tradition of large consortia of private individuals forming to try and solve problem #1, in recent years these have even tended to win. The trouble then is what happens to the money that was pledged by losers: at lca2011 (and I think lca2010 too, but I wasn’t there) bids aren’t revocable. The donated money stays donated, the only question is whether you get a prize associated with it.
So far so good for money. And now for entertainment, as Rusty posts. The trouble with lca2011 was that the auction consisted of people walking up to laptops and having their donation amount entered and associated with their team. Running totals were displayed on a graph, but spectacle was lacking.
The ritual humiliation of Linux celebrities does have something in it. But, no more screaming for people’s beards. I think it would be much more appropriate, and probably fun, to organise something in advance to occur at the dinner, with celebrities volunteering. The closest model would be lca2004′s dunking of Linus Torvalds (which was organised in advance, the pressure placed on Torvalds to participate I can’t speak to but he gives the appearance of generally enjoying some mild organised humiliation for the benefit of charity).
Say, as an example, that five developers compete to throw three-pointers (actually, this is probably too hard, in addition to being difficult to stage at a dinner, but never mind). Then there’s a very short pre-planned set of auctions for things like being able to take steps forward to start with, extra shots, probably culminating in the right to substitute, together with a simple “highest amount, yay!” kind of contest. At least one or two bids to allow your celebrity to increase the challenge facing an opponent. Probably five rounds of shots total with bidding in between. You could probably solve some obvious problems (like everyone backing Torvalds or betting against him or whatever) with simple transparent manipulation: Linux Australia increasing their matching donations when tables back their assigned celebrity, or something.
Finally, since this is a developer conference, there should be some kind of application allowing people to pledge using their phones from their tables.