After the first paragraph, I was going to recommend he dabble with MSTR since he has experience with stocks, options and derivatives. Sounds like he is already doing this and that he has done his homework with Saylor strategy.

I wouldn't try to argue with him because he already has a plan or strategy.

Some or most people view bitcoin as a vehicle for huge capital gains, short and long term.

Think of it this way, you and your friend will have a lot to talk about (friendly and civil discourse)! On X or Twitter there is a huge community called Irresponsible MSTR. Your friend should follow a user named Punter Jeff.

Disclosure: I own btc and MSTR