Why you want your manager, your business manager, and your booking agent to work for different agencies.

Young Buck’s not having a great year.

In the wake of his recent arrest, we’re learning more of the details about his money troubles, and the feud with 50 Cent over an unpaid $300,000 loan. He owes the IRS even more than that, and his record label’s already filed a $10 million claim with his bankruptcy trustee.

According to news reports, his lawyer traces most of Young Buck’s money troubles to a locked up relationship with a single agency that handled his career management, his booking, his recording, and his business management. Oh, and all of those folks were on 50 Cent’s payroll.

As I wrote about for the new edition of Music Management for the Rest of Us, it’s tough enough to find one person to help manage the business side of your music career, let alone three. But the roles are all very important, especially when each person in the relationship has a vested interest in keeping the others honest. A booking agent will be the first to complain if a business manager can’t keep the books straight. A manager will cry foul when a booking agent starts puffing up numbers to increase commission. And a good business manager is your only line of defense if your manager or your booking agent decide to start grabbing extra cash from the bank.

I can tell you from experience, it’s no fun being on the other side of this equation, either. At various points in my own career, I’ve wound up handling both booking and management duties for clients, and it sucks. As a manager, you want to focus on long term strategy. As a booking agent, you want to jam out as many paying gigs as possible. It’s hard for an honest person to reconcile the duties, but when someone handling both roles decides to turn against you, they already control most of your income and your connections. Layer the business manager duties into the mix, and you’ve got a recipe for disaster.

If you’re Young Buck, oblivious to your real financial situation, submitting a $1 million recording budget for your next album doesn’t even sound like a bad idea. Finding some “no” men willing to fight for him could have kept him from making some major career (and legal) mistakes.