How Jessica Simpson Really Lost So Much Money

As the old saying goes, the higher you climb, the harder you fall. And when you're a multi-hyphenate singer, actor, and fashion mogul worth billions, there are plenty of ways your fortune could fall out from under you — a too-lavish lifestyle, a series of poor choices, or, in Jessica Simpson's case, a business acquisition turned bankrupt. 

The "Dukes of Hazzard" star explained in a tell-all interview with Bustle that she was forced to make a difficult decision regarding her billion-dollar fashion brand, the Jessica Simpson Collection. When her business relationship with licensing company Sequential Brands, which bought a majority of JSC in 2015, turned sour, she either had to give up her dream of continuing the company, or liquidate her assets to buy back full ownership.

Ultimately, the "With You" singer chose the latter, liquidating her stock portfolio and putting her California home up for collateral to regain full ownership of the Jessica Simpson Collection in 2021. While this financial rearrangement has been difficult and has caused her to lose a lot of money, Simpson told Bustle that she — with the help of her mother, Tina Ann Drew — believes she's made the right choice.

The story of how Simpson lost so much money is not uncommon in the business world: first, a business buys a brand (in this case, Sequential bought the Jessica Simpson Collection). Then, the larger business attempts to cut costs at the expense of its acquirees. Often, this means the dissolution of the company — unless, of course, you're dealing with a brutally honest firecracker from Texas like Simpson.

The singer recalled watching Sequential move closer to bankruptcy following the devastating effects of the COVID-19 pandemic on brick-and-mortar-dependent brands like hers. The licensing company even attempted to furlough seven of the ten team members that headed the JSC, including Simpson and her mother, Tina Ann Drew, which proved to be the final straw. She decided to fight for her namesake company both for herself and for her three children. "If they don't see me following my dreams and fighting for what I believe in, they'll never do it themselves," she told Bustle. 

Simpson and Drew still owned 37% of JSC, and in an attempt to save their company from going down with Sequential, they bought the rest of their shares back for $54 million in the summer of 2021, just months before Sequential Brands would file for Chapter 11 protection, according to Financier Worldwide.

The Jessica Simpson Collection might boast her name, but the process for Simpson to buy back her company was not easy. She told Bustle that she had to liquidate her stock portfolio and put her gorgeous mansion up as collateral. The mother-daughter duo acquired a $67.5 million loan from Second Avenue Capital Partners in May 2022, per PR Newswire, which will kick start their next endeavor: an original JSC hair care line. 

As Simpson works to revive her brand, she's not afraid to admit that she's had to lean on her mom for financial support. Drew told Bustle that she was willing to do it, citing her role as Simpson's mother first and foremost, but she did have a few caveats. "In buying the brand back, I told her, if you're sure you want to do this, you're just going to have to tighten up your belt a little bit. You're going to have to not live not quite as extravagantly."

And that's where Simpson finds herself today: tightening the purse strings, keeping her head down on expanding the JSC brand, and dipping her toes back into the musical world. She might be navigating a valley right now, but we have no doubt that there is plenty of fight and much more of the stunning transformation of Jessica Simpson that we still have yet to see.