Dame Dash has had big deals and little things, but his business model is one most can't imitate. "People say never put up your own money. I'm saying put your own money up," he tells VIBE in part two of My Philosophy. "Work harder than everyone, be patient and just know that if you're going to do something on your own, you're gonna have to feel some pain."

It's his flair for risk-taking that has also hurt the Roc-A-Fella co-founder's wallet. Back in May, he filed a five-page court document detailing the extent of his debt, owing $2 million in IRS taxes and apparently abandoning his upstate New York estate. Still, his hustler's mentality has stayed in tact and owning his investments. However, it hasn't stopped him from falling victim to funny-style characters.

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