Over the past eleven years, singer/songwriter Cole Swindell has made an indelible mark on country music. His expansive catalogue of music has racked up billions of streams and 13 No. 1 hits, so far.

Cole Swindell has made writing chart-topping hits look easy, but he knows the real story is far from it. Staying humble isn’t hard for Swindell, who spent three years selling T-shirts on tours with ...