If your startup is going bankrupt, a good rule of thumb is to not flaunt piles (and piles) of cash on your social media. Take a lesson from rapper Curtis Jackson III (better known by his stage name "50 Cent")--who did just that.

In July 2015, the 40-year-old entertainer filed for Chapter 11 bankruptcy protection. Jackson came under fire last month for flashing his cash on social media. On Instagram, the rapper posted a photo of himself with piles of cash that spelled out the word "broke."

In another, he wrote, "My crib is almost finished in AFRICA," along with a video showing the home's exterior. To some, it indicated that he may own a property in Africa. Jackson's creditors, who first brought the posts to the court's attention, said that they were "contemptuous" of the bankruptcy process. 

The 40-year-old entertainer said in a court filing late Tuesday that the stacks of cash in the photos are actually prop money, which is specially made for the studio lighting used in filming music videos and photo shoots.


On Wednesday, Jackson was ordered to explain those images in court. Connecticut judge Anne Nevins insisted his activity had raised some concern over "allegations of nondisclosure and lack of transparency."

Jackson did not speak directly to the issue when summoned, though he elaborated in the court filing: "Just because I am photographed in or next to a certain vehicle, wearing an article of clothing, holding a product, sitting next to what appears to be large sums of money or modeling expensive pieces of jewelry does not mean that I own everything in those photos," he wrote.

The rapper claims to have assets of just under $20 million, and liabilities of $36.09 million. (His major expenses at the time of filing included a $7 million mandated payment to Lastonia Leviston, a Florida woman who said that Jackson had published a sex tape of her online without permission, as well as a soured headphone deal costing him $18.4 million.)

Jackson's reps aptly noted that hip hop culture places a high premium on wealth and masculinity, one which rappers often feel they must uphold on social media. Patrick Neligan, Jackson's primary bankruptcy lawyer, said Wednesday that this culture is "aspirational." Many of Jackson's fans, he added, "come from poverty. They want their favorite rapper to be rich. Money is important." 

"Since the explosion of social media, I have maintained a strong social media presence that is consistent with the public persona of '50 Cent,'" Jackson wrote. 

Still, business owners know well that social media can be both a blessing and a curse when it comes to crafting a brand. A poorly delivered pun, or piece of humor misinterpreted, can have dire consequences.

"Twitter is for business. Instagram is for business. You never know when someone is going to take a picture of you. It's a very public industry. You have to know you always have to be on," noted Shanti Das, a hip-hop industry analyst and music executive, speaking at the Berklee College of Music in 2013.

Jackson refused to provide verbal comment following the proceedings yesterdays, however he did take to social media once again. On Instagram, he posted a photo of himself with stacks of cash flowing from his pants, with the caption: "For some reason people love me. I went to court today and all I felt was love. They asked me about money I said I ain't got none,but if you want some m&m's here ya go. #EFFENVODKA."