The other problem is that it is interchangeable with many other jokes of the same flavor, ie, they were buying Facebook private shares, getting into the LinkedIn IPO, et cetera. This is a tip off that even if it's funny it might not be relevant.

See also the South Park critique of Family Guy.

Saying they were doubling down buying shares in Hilton and Motel 6 would at least have been marginally on topic. But still a bit obvious, right?