Growing up poor in Philadelphia, Troy Carter hatched an escape plan: “I was going to become the biggest rapper in the world. There was no plan B.”

It didn’t work out. His group, 2 Too Many, flamed out not long after he quit high school to pursue his dream full-time.

However, because of that fast failure, Carter, now 46, took a different course that led him to where he now sits: in a $7m (£5m) Spanish-style estate above Beverly Hills.

Short, slight and bespectacled, Carter glides between very different worlds.

As Lady Gaga’s first manager, he helped her go from obscurity to stardom. He is a tech investor, having placed early bets on Uber and Dropbox. He handles Prince’s musical estate, including a vault full…