Amongst people who think probabilistically, this isn't a weird statement. It's a very low precision guestimate. There is a qualitative difference between 50-50, 90-10, 99-1 etc, and it's only their best guess anyway.
Are these based on data? No, they're rhetorical tools used to sound quantitative and scientific.
Nobody will be applying the calculus of probability to these meaningless numbers coming out of someone's ass.
And most importantly, is he himself willing to bet a significant fraction of his fortune based on these socalled probabilities? I don't think so. So they're not probabilities.