Armando Christian Pérez —better known as Pitbull— is a rapper, entrepreneur, motivational speaker, brand ambassador and has a whole host of other job titles. As his nearly two-decade-long career has diversified, his image and brand have solidified. He rose to prominence off bilingual records hits like “Culo” and “Toma” in the early aughts and became a household name thanks to wedding and quinceañera classics like “Give Me Everything” and “Time of Our Lives.” Today, the Latino demographic that helped catapult Pitbull to the top music charts is facing greater open discrimination than at any other point during Pitbull’s career. During a day with Pitbull, the Cuban-American entertainer opens up about his thoughts on President Trump, the state of immigration, why he won’t stop making music with Chris Brown, and how country music is not just for white folks.

Also, a new “How I Made It” segment featuring Chicago singer, songwriter Kaina Castillo.