The woman who managed Tupac Shakur and Earl Sweatshirt two decades apart
Not many rap fans will necessarily have ever heard of Leila Steinberg, but, without her pivotal, decades-spanning influence, the careers of two significant stars may not have played out as they did.
Steinberg helped Tupac Shakur to get his career up and running in the late 1980s and into the early ’90s, before, 20 or so years later, repeating the trick with a young Earl Sweatshirt. Within two different generations of hip hop, then, her role has been vital.
Steinberg, as a 25-year-old, first encountered Tupac when he was just 17. She was running poetry classes at the time, and Pac was one of her students. The pair of them got on very well, and she was apparently a great influence upon the development of the young Pac’s writing skills. But the relationship worked both ways, as she learned a lot from him, too.
“I would say Tupac was an amazing teacher for me, as one of the first artists I worked with, because he was so brilliant and he read so much,” Steinberg noted during an appearance on NPR in 2015.
As Pac built up his reputation as a young rapper, Steinberg served as his manager and mentor. She stepped away from the role around ’93, when Pac’s career was exploding, and his management required more than what she could offer.
For many years, Steinberg didn’t take on another management role with a musician, but she was drawn back into that world when Earl Sweatshirt’s mother reached out. Earl had begun releasing music while he was still a teenager, but, away from the growing success of his young career, he was still getting into trouble.
His mother sent him to a boarding school in Samoa following the release of his 2010 mixtape Earl, where it was hoped that adjustments could be made to his behaviour. The rapper, despite his obvious talent, needed help, so that’s where Steinberg, who knew his mother and had this experience working within the music business and with young people, came in.
“I came in as a parent, not as a music businessperson,” Steinberg reflected on her role in the young Earl’s life, “And really, the plan was that I would help him transition into a healthy life back in LA pursuing his dream, but not that I would be really active in his business.”
Steinberg did, ultimately, become more involved in the business side of things, becoming Earl’s manager and helping to guide him through the early stages of his career, just as she had done for a young Tupac so many years beforehand.