Let Your Light Shine' was influenced by artists such as Peter Tosh, Anthony B, Sizzla, and Bob Marley and released by Iakopo independently on 12 December 2006. The singles "Let Your Light Shine" and "Love Jah" made it to the top of reggae charts in the US, Hawaii, Polynesia, Asia and Europe. This success led to a record deal with 1980 Entertainment, as well as Iakopo sharing the stage with many influential reggae artists. After an independent tour throughout Hawaii and West Coast America in 2007, he co-headlined the 'Summer Massive Tour' in 2008, alongside Tribal Seeds. He also was the opening act for Half Pint's 2008 concert in World Beat Center, San Diego, CA  In 2009 he toured as support for Israel Vibrations, Junior Reid, Midnite, Collie Buddz and Messenga Selah.

While touring, he wrote the album Born To Win. On this, Iakopo focused on his island roots, as can be heard on the single Heart of Polynesia. This single was another No. 1 hit on Hawaiian radio stations, as well as winning the International Music Video Award for World Music 2009. A dispute led to Iakopo splitting with his label and deciding to start writing music under his own name.