Unless I read it wrong, it sounds like this guy did not get it paid for by his employer - he runs multiple companies and is an angel investor with clearly deep pockets - and I have people talking about it being an investment in their careers. He could be using it support his businesses, yes, but that needs to be clarified and is still not a situation most people find themselves in.

This is not a straightforward business expense conversation IMO. Otherwise yes I do agree with you. A company should invest in supporting local models for their team.