The example he gives of writing he would sign is a blog post. The blog post is already authenticated because it’s on avc.com. Fred Wilson has the tokens, social authority etc to ensure what shows up there under his name is from him. Technically speaking, it was already signed via TLS when sent to my web browser. It is also unclear how ChatGPT potentially breaks this sort of authentication.
Again, what is the threat model, what is the problem being solved? It seems like ChatGPT is much more likely to be used by someone imitating themselves out of laziness (“I don’t feel like writing this blog post today”) than to imitate someone else out of malice and this scheme does nothing to solve it.
I suppose someone could make a HN or Reddit account and pose as Fred Wilson and then ChatGPT makes it more credible. But are HN or Reddit going to allow GPG-style signed messages? Seems more likely, if this became an issue, they would move to usernames expressly tied to visible email addresses or domains that could be authenticated by receiving an email, adding a DNS entry, OAuth etc.