If you have the bandwidth, there's plenty of benefit to consuming counter points of view even if only to have a better understanding of what you stand against. I would recommend against reading someone like Ben Shapiro because, awful writing aside, conservative pundits are mainly grifters who make a living selling snake oil to 'temporarily embarrassed millionaires'. Someone like Peter Thiel will give you a much clearer insight into what the capitalist class actually thinks.

Also, concerning the prince: while it's not really a "leftist" text it's always worth mentioning that there's an interesting debate among historians regarding it's purpose/role from Machiavelli and whether not his one book about "how to be a sith Lord for dummies" was actually written to be subversive.