His father died months after he was born,[5] while his mother was incarcerated for six years in Argentina when Castillo was around the age of eight, eventually relocating to San Juan, Puerto Rico where he lived with his grandmother.

[6] In 2004, just before his twentieth birthday, Castillo met with another young reggaetón musician born in New York City by the name of Austin Santos—better known to the public as Arcángel—and the two decided to form a duo, Arcángel & De la Ghetto.

[7] The pair debuted with their single "Ven, Pégate", which was featured on Naldo's mixtape Sangre Nueva, in 2005.

From there, Castillo was signed to Zion's label, Baby Records, and immediately began to make music.

In 2006, De la Ghetto officially began his solo career, appearing the following year on two hit singles, as well: a remixed version of "Siente el Boom" by Tito el Bambino, plus a collaboration with Randy called "Sensación del Bloque", which has been viewed on YouTube over 200 million times as of July 2023.