Earlier quoted context omitted.
Complicated question. Dismissive comments about new things bother me partly because there's an asymmetry that seems unfair. It's so risky to create something new, and so easy to dismiss it. At their worst, the people making such comments are like schoolyard bullies picking on someone who tries to do something different. This particular case is very mild-- more confused than dismissive really. It just struck me as fun…
I think it was valid critique. (Something I am sure you give the companies you fund.) It's not always easy to provide critique without knocking the cause - But I understood that's how jug6ernaut meant it. If I were to buy a tshirt for HN, which I might possibly do - I'd want it to show off a message rather than it looking like it could be for anything. This doesn't feel personal to the brand to me – I could buy this…
You're mistaken about the design though. It's both funny to make the design so minimalistic, and yet simultaneously a pretty bold assertion of brand power. And since we don't want HN to grow fast, we don't need to send any messages to anyone who doesn't already recognize the shirt.