50 Cent Offers His Two Cents on Investing and Lingerie

NEW YORK ( The Street) — Get rich or die tryin’.

That’s the motto that first catapulted 50 Cent onto the Top 40 charts. As recently as May, the rapper-turned-entrepreneur boasted a net worth of $155 million, according to Forbes estimates. Yesterday, just days after he was ordered to pay a woman $5 million for posting a sex tape online without her consent, the 40 year-old filed for Chapter 11 bankruptcy in a Connecticut court.

50 Cent reported his estimated assets and liabilities each at between $10 million and $50 million.

In apparently happier times, earlier this summer, the recording artist born Curtis James Jackson III could be found strutting the red carpet to promote Power, a Starz (STRZA – Get Report) series in which he’s an actor and executive producer. At the time, 50 Cent was loaded with investment tips.

“See, a lot of the projects I’ve involved myself in, I took the time to do the due diligence to make sure I’m safe,” he said of his entrepreneurial endeavors during an interview held just off the red carpet.

Following his chart-topping hits, Jackson has had highs and lows as a business mogul. Arguably, his best bet was a deal with Vitamin Water, which netted him $100 million when it was sold to Coca-Cola (KO – Get Report) in 2007. But investments in a clothing line, headphones and vodka got tangled in litigation or failed to catch fire in the same way. The bankruptcy filing, his lawyer said in a statement, is meant to safeguard ongoing businesses.

Must Read: 50 Cent’s Bankruptcy Curse: 7 Other Rappers Who Went from Boom to Bust

“The filing allows Mr. Jackson to reorganize his financial affairs, as he addresses various professional liabilities and takes steps to position the future of his various business interests,” said William A. Brewer III, partner at Brewer, Attorneys Counselors and counsel to Jackson in the statement. Separately, the rapper placed his boxing promotion company, SMS Promotions, in bankruptcy in May.

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