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If you note, I put “businessman” in quotes for both of them because it isn’t the correct term for either of them. It isn’t the correct term for Taylor because it is the wrong pronoun, and it isn’t the correct term for Trump because he seems incapable of running a successful business. It was an intentional construct for ironic parallelism, not an oversight.

If they don’t have to worry about guns, then why do they have guns drawn?

Reagan was at least governor of California prior to running for president.

The argument that “you shouldn’t vote for someone just because your favorite celebrity endorses them” seemed like a much more credible argument before the 2016 election when the winning candidate essentially won by literally being a celebrity.

Prior to 2016, Trump was probably best known for being the host of a reality TV show, and being a “businessman”. Taylor Swift is definitely better known, and you could also make a solid argument that she is a better “businessman” as well.