He's a salesman pushing an entire industry who regularly receives special treatment and access from LLM vendors. The fact that he's open about getting these favors and subtle enough to sprinkle his salesmanship with a thin veneer of skepticism and plausible deniability doesn't make it any less of a grift.
I'm obviously biased when it comes to FOSS foundations, but Simon is also a member of the board of the Python Software Foundation, which is not nothing in terms of looking after our craft.
The LLM stuff feels minor in comparison, even if it may be what HN knows him for. It's certainly not the same level of achievement as your average bargain bin AI rambler in your LinkedIn feed.