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I think for the fundraiser, Lightcone should sell (overpriced) lw hoodies. Lesswrong has a very nice aesthetic now, and while this is probably a byproduct of a piece of my mind I shouldn't encourage, I find it quite appealing to buy a 450$ lw hoodie, even though I don't have that much money. I'd probably not donate to the fundraiser otherwise. And if I did, I'd donate less than the margins on such a hoodie would be.
Yeah, I've been thinking about doing this. We do have a reward tier where you get a limited edition t-shirt or hoodie for $1000, but like, we haven't actually designed that one yet, and so there isn't that much appeal.
If we do a merch store, I would definitely want things to be high quality. Slightly ironically I can't guarantee as much for the donation tiers (since we already promised the t-shirts at least and we might not find a good manufacturer), but I will definitely still try to make it good. I can't really guarantee it in advance, based on my experiences with the stuff.