Timbaland

Timbaland's production discography reads like a greatest hits of the 2000s: "Cry Me a River," "SexyBack," "Apologize," "Are You That Somebody," virtually every Missy Elliott hit. He was arguably the most in-demand producer of his generation. And yet, at $10 million, he's worth 50x less than Dr. Dre.

The gap comes down to one thing: business ventures. While Dre was building Beats Electronics, Timbaland was collecting production fees — which, while substantial ($50,000-$500,000 per track plus royalties), are fundamentally service income. You get paid per project. When you stop producing, the income slows. Production royalties from older songs generate ongoing revenue, but it's a trickle compared to owning a product company.

Timbaland also faced financial difficulties including a reported $4 million dispute with the IRS and losses from failed business ventures. His more recent Beatclub platform — a marketplace for beats and production tools — shows he's learned from watching Dre, but it's still in early stages. At $10M, Timbaland is comfortable but not wealthy by industry standards. His story is the perfect illustration of why producing hit songs and building hit businesses are completely different skills.