His journey began on YouTube. He put his 10,000 hours in live looping with his saxophone, beat machine and keyboard. Masego used to rip beats from SoundCloud's future beat and house producers and add saxophone over them then head to Instagram and dedicate the song to a curly hair beauty from his explore page. His soulful singing and his jazzy personality colored every track and heart and caught the attention of many producers like Kaytranada, Sounwav, and new greats like KRS and Medasin.
The Pink Polo EP with Texas Producer Medasin was the result of his SoundCloud antics. Their song Girls That Dance launched Masego and the TraphouseJaZZ band on a world tour. Japan, France, England, Germany and more got to experience Masego's unique live show. Girls that Dance found it's way to Jazzy Jeff who later reached out and invited Masego to his modern day XMen Mansion school for the gifted.
Masego nurtured his superpowers in Jazzy Jeff’s pool house, where legendary musicians were constantly pouring in. Jazzy Jeff's experience inspired him to work on hundreds of records. Masego decided to drop another project. He called it Loose Thoughts, a project full a energetic singles, more developed song writing and his beloved saxophone.