In 1989, in Marin City north of San Francisco, a 17-year-old showed Leila Steinberg his poems. She listened and became the first person to systematically push Tupac’s career forward.
How Writing Classes Became “The Microphone Sessions”
Steinberg was born in Los Angeles in 1961 and grew up in South Central. As a dancer, singer, and educator, she led writing and poetry classes for young people, many of them from difficult backgrounds. Tupac joined in 1989, and the two connected immediately.
According to her, he lived on and off with her and her family for about two and a half years, reading and writing under her guidance. Those meetings grew into the workshop they called “The Microphone Sessions”: poetry, rap, singing, and theater in a circle. Many of the poems published in 1999 as the book The Rose That Grew From Concrete originated during this time.
Manager at Tupac’s Request: The Path to Digital Underground
At Tupac’s request, Steinberg became his manager. She supported his group Strictly Dope with rapper Ray Luv; she is said to have brought the two together. In addition, she brokered the connection to Atron Gregory, the manager of Digital Underground.
When Tupac went on tour with Digital Underground in 1990 as a roadie and dancer, his actual career began. Their business collaboration ended in 1993; Steinberg remained a friend and confidante until his death.
Workshops in San Quentin and the View of Tupac Before Fame
Steinberg expanded her work with young people further. Through the organization AIM4TheHeART, she offers writing workshops, for many years also at San Quentin prison. As a manager, she later worked with, among others, the rapper Earl Sweatshirt.
In the Tupac biopic All Eyez on Me (2017), she was played by Lauren Cohan; in the FX docuseries Dear Mama (2023), she spoke for herself. She is among the few people who knew Tupac before he became a rapper and witnessed his evolution from poet to musician up close. She stands for Tupac before fame: a young poet who learned to turn anger into language.