This line ties into the last. Checkers, a simple game, is being compared to selling out. Chess, a more complex game, is being compared to hardwork, which takes skill, planning, and time. B.o.B is playing chess in this rap game (staying true to oneself), not checkers (selling out).
The line is also a reference to the vast hip-hop collective founded by B.o.B’s friend and labelmate Lupe Fiasco, “All City Chess Club”, of which B.o.B himself is a member. B.o.B had used a similar line in the All City Chess Club song “We Beamin'”
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