Big Sean hits us with not one, but two songs in the same night. Just hours after debuting the inspiring “One Man Can Change the World” featuring Kanye West and John Legend, Sean Don reunites with his “Beware” collaborator Jhené Aiko on “Win Some, Lose Some.”

The 26-year-old MC gets real and raps about being a role model, his ex (“I always thought my last girl was supposed to be my last”), and turning his mom’s hooptie into a Cadillac (“People thinkin’ I’m rich and I wish they knew that / I been signed for four years and I’m just able to do that”), while Jhené adds her sultry vocals.

Additionally, the two have collaborated on another song called “I Know” for Sean’s album Dark Sky Paradise (due Feb. 24).

If you pre-order the album on iTunes, you will receive “Win Some, Lose Some” as an instant download.