Daughter of jazz bassist, Pops Kahakalau (a.k.a Bob Carter) and granddaughter of Hawaiian musician Tutu Kahakalau, Robi was born and raised in Germany and moved to Hawaii at the age of 17. When she moved to Hawaii her interest in Hawaiian music led her to study the language to learn what the songs were talking about. In 1988, she graduated from college with a degree in Hawaiian Language.
In 1995, following several successful years with the Hawaiian Style Band, Robi set out on her own and released her first solo album, entitled Sistah Robi, with featured artists Roland Cazimero, Ernie Cruz Jr., Troy Fernandez, Bryan Kessler, Sean Na'auao, Jeff Rasmussen, and Fiji. The album was awarded the 1996 Hoku for best Island Contemporary Album.
Robi's second album, 1997's Keiki o ka `Aina (Children of the Land), reveals Robi's love for the children, the land, and life itself. Featured artists are Michael Grand, Fiji, Sean Na'auao, and Dave Tucciarone. Also included are the Ka'au Crater Boys, The Makaha Sons, Cyril Pahinui, BB Shawn and a chant by Kekuhi Kanahele.
Released in 2000, Robi's third album features songs ranging from Hawaiian, to reggae, blues, jazz and R&B, with lyrics in English, Hawaiian, Tahitian and French. Among guest artists are The Makaha Sons, Kapena, Lehua Kalima of Na Leo Pilimihana, Sakiusa Bulicokocoko, Ernie Cruz Jr., Eric Gilliom, Shawn Ishimoto, Sean Na'auao, and Jeff Rasmussen.
Before launching her solo carrier, Robi performed in the Hawaiian Style Band along with Wade Cambern and Bryan Kessler. 1992's Vanishing Treasures won the Hoku Award for Island Contemporary Album of the Year.
The Hawaiian Style Band's second release in 1994 matched the success of their first album and also received the 1995 Hoku Award for Island Contemporary Album of the Year.