system
A chat on subreddit /r/me_irl
human
It's closer to 50/50 than you may think.  The secretary is going to balance the time they need to spend to find out if you are actually someone worth an actual response vs 100$ of a billionaires money.

They won't be buying you a boat, but the clerk is likely to decide to send you nice bath towels rather than bother researching if you are not worth the response.

You are basically gambling 36 cents and 5 min of work that the clerk doesn't care about 100$ of a billionaires money.
gpt
How does any of that make it a 50/50 chance