One way to prove that he truly doesn't mind looking stupid would be to list times when he risked looking stupid... and it turns out he actually was. It's happened to all of us though we dont like to admit it. I'm sure it's happened to him too and I looked but I didn't see any of those examples listed. Giving only examples of when people thought he was dumb and it turned out he wasn't... that's kind of just a roundabo…
Learning isn't a straight path. It's unusual to not veer off and misunderstand something for a while, during which time others might be right to assume you are "stupid".
The willingness to look stupid will sometimes reflect that you are, in fact, actually stupid. A lack of any examples in this category makes this post read more like a humble brag.