Who Would Be in Your Entourage? (And Could You Trust Them?)

Watch HBO’s popular show “Entourage,” and you can get posse envy. Read Hannah Karp’s story today about pro athletes’ real life entourages, and the business headaches they can cause, and suddenly doing-it-yourself doesn’t look so bad.

Photo from hbo.com/entourage

Ms. Karp describes how boxer Oscar de la Hoya is saving about $400,000 a year after giving the boot to 10 entourage members, most good friends. One charged $2,500 for attending public events. Other athletes are quashing lump-sum payments and putting friends on payroll. The reason: It helps with taxes.

For anyone running their own show, there will always be issues with figuring out whom to hire into your inner circle, how much information to trust them with, and how to compensate them fairly without getting taken for a ride.

When you’ve got millions in the bank, it’s easier to get lax. MC Hammer’s 200-person entourage helped eat up most of his fortune.

It helps to pick the right people. When Steve Demos of Silk soy milk fame started his newest venture, he mostly hired his old management team. That’s something many serial entrepreneurs do. It’s also about winnowing down employee theft. And keeping people on staff informed about what you want—and don’t want—from them with training.

Readers, have you ever been burned by an employee you kept close? What did you do? Also, just for fun, if you could hand-pick your own “personal entourage,” what tasks would you want them to perform?

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