How Jessica Simpson Almost Lost Her Name And Her Billion Dollar Empire

The pop star’s billion-dollar fashion brand fell into the hands of the wrong company. After a two-year battle, she finally bought it back. How Jessica Simpson Almost Lost Her Name And Her Billion Dollar Empire

Of all the ways Jessica Simpson had imagined taking back control of her fashion empire, lying on a hospital bed with severe bronchitis, on a breathing machine, while 34 weeks pregnant with her third child, a daughter, was not one of them. “Her oxygen levels were dropping.

I couldn’t breathe,” recalls Simpson of the harrowing, rather impractical moment in early 2019 when she and her mom, Tina, president of the business, decided to initiate a takeover bid. “I was 260 pounds. She was a very big baby. We were like, ‘Just take her out.’ ”

Her daughter Birdie didn’t end up being delivered that day (doctors were able to stabilize her), but that moment did mark the beginning of a two-year battle for control of Simpson’s namesake brand, the rare celebrity line to break $1 billion in sales.

“We’ll borrow against our homes,” says Simpson of her resolve. “Even if I have to go live in a little, tiny place in Ireland, I will.”

When Simpson started the line in 2005, she was an improbable apparel mogul. The gospel-singing daughter of a Baptist pastor, she first surfaced on the pop-music scene in the 1990s, a new breed of sexy teen blond belters alongside Britney Spears and Christina Aguilera.

Although she had the vocal chops, it was the pioneering 2003 hit MTV show Newlyweds, a voyeuristic romp through the then-23-year-old’s new marriage to her boy-band husband, Nick Lachey, that vaulted her into the pop-culture firmament.

Those who’d written her off as merely a ditzy entertainer became converts. Her viral malapropisms, frank charm, and sexy Texas style drew an Instagram-like following years before the social platform even existed.

Almost two decades later, Simpson had reached the stage of celebrity where she was mostly famous for being famous. After a divorce, she’d married former NFL player Eric Johnson, but over the years she’d developed an alcohol addiction.

By 2017 the mother of two young children was carrying a glittery tumbler of vodka and flavored Perrier everywhere, sipping from it mornings before school drop-off.

After a drunken Ellen appearance, followed by a blackout at a family Halloween party, she finally got professional help. In 2019 she was sober and had millions of actual Instagram followers, but she hadn’t recorded an album in almost a decade.

Throughout all of this, Simpson’s business had been one of the few constants. She didn’t have the can’t-stop-won’t-stop drive in her bones, hatching companies and making investments the way Jay-Z eventually would.

She wasn’t going to build a wellness empire like Gwyneth Paltrow with Goop Inc. or court venture capital investors like Jessica Alba with her baby-products line.

She wasn’t going to introduce a tequila brand like George Clooney, who sold it to Diageo Plc for some $700 million after four years.

And she certainly wasn’t going to cycle through businesses as if they were shoes like Kim Kardashian, who seemed to unveil a new line or deal every year or so until finally building cosmetics and shapewear companies now worth a combined $2.6 billion.

Simpson, though, predated all of them, in 2005 taking one swing at a very conventional business with a very conventional strategy: She’d introduce a clothing brand for Middle America.

Teens and their moms who wanted to shop at Macy’s or Dillard’s so they could dress like Jessica Simpson could suddenly afford to do so—some $80, these days, for a leopard-print sweater or $110 for wedge ankle boots.

Rather than build a company that actually made the stuff, she’d license her name to the best manufacturers out there, which would then design and produce the Jessica Simpson Collection’s products, including apparel, perfume, and handbags.

Tina, who’d largely been a stage mom, would run the company, with the help of a shoe-business whiz who oversaw the licensing and took a stake in the business in 2005.

Oddly enough, the formula not only worked, it outlasted the fashion lines started by many other celebrities—Mandy Moore, David Hasselhoff, even style maven Sarah Jessica Parker.

Eventually, the brand did $1 billion at retail, with Simpson appearing on the cover of New York magazine as “The $1 Billion Girl,” surprising everyone that the seemingly not-too-bright singer was actually a very clever businesswoman.

“To put that figure in context,” the article read, “it means Jessica Simpson is doing roughly the same volume in sales as Michael Kors.”

But soon after her brand’s ascent was being hailed publicly, a slow unraveling began in boardrooms, on earnings calls, and on profit and loss sheets.

In 2015, after the Simpsons’ business partner had died from cancer, they cut a deal with a different kind of company with a charismatic young chief executive officer who intended to expand the line into a “$2 billion to $3 billion operation,” as Women’s Wear Daily reported at the time.

But the company, Sequential Brands Group Inc.—more of a licensing financial middleman than creative partner—was soon in over its head. By 2019 it had become clear to the Simpsons that Sequential was actually in deep financial trouble and had no intention of expanding their business. They were watching their empire slowly die.

In that hospital bed, Simpson had finally had enough. The way Sequential was structured, the whole point was to tap a brand until there was nothing left.

The business wasn’t unlike the celebrity game in so many ways, a different version of what she had experienced her entire life, like when her dad pushed her to switch from gospel to pop or when a record executive instructed a teenage Simpson to lose 15 pounds, so she took diet pills.

“My name was on it,” Simpson says of her business. “I don’t ever move away from my name.”

So Simpson told Tina and another Collection executive to approach Sequential to buy back the brand. It would require two years of negotiating with the company, which eventually filed for bankruptcy and was forced to sell everything it owned for parts.

“We’re ready to go into the trenches,” Simpson says over Zoom this fall, sitting on a cheetah-print chair in front of her fireplace in Los Angeles, waiting for the deal to finally go through. “Pay it all back and earn it ourselves.”

Ten years before Simpson fired him as her manager in 2012, her father, Joe, pitched MTV a docuseries about his famous daughter. Growing up, Simpson had moved 18 times as her parents hustled for work.

Joe, a Baptist preacher, sold postage meters for Pitney Bowes Inc., while her mom ran Heavenly Bodies aerobics classes at churches—that is, until Joe realized it was their little blond girl with a big voice who could bring in cash.

Tommy Mottola, the powerful record executive who later signed Simpson, told Vanity Fair she was different than the new crop of teen-girl pop stars in that she could actually sing. “I was about to become the family business,” Simpson wrote in her 2020 memoir, Open Book.

When Newlyweds made its debut in 2003, it was supposed to run for only six episodes, but it ended up becoming a three-season cultural phenomenon. At a time when the most intimate you could get with a celebrity was on the pages of Us Weekly, Simpson did something radical.

Instead of wearing layers of makeup and midriff-revealing getups, she would wander around her house in a Juicy Couture sweatsuit or throw a gigantic fringed scarf over her shoulders while attempting to cook.

In a moment that went viral before viral was viral, Simpson plopped onto a couch, poking at a bowl of something with tuna. “Is this chicken what I have, or is this fish?” she asked her new husband, Lachey. “It said ‘Chicken by the Sea.’ ”

Simpson got publicity—bad, good, everything in between—transforming her from a fading pop star into a relatable comedienne. Her debut album years earlier had charted at No. 25, and the follow-up fizzled; when she put out an album mid-Newlyweds, it went triple platinum.

Simpson was flooded with appearance requests and endorsement deals. (Meanwhile, the couple divorced in 2006.) Suddenly stay-at-home moms, tweens, everyone seemed to see themselves in Simpson: “I am you,” they’d tell her at her appearances.

Then Simpson noticed something—they started dressing like her, too. “People would be coming in a shawl,” she says. “And everybody was definitely wearing the Juicy sweats.” For the first time, her fans were responding to her, not to some image that managers or executives had engineered.

Simpson and her mom, who’d handled the pop star’s styling and photo shoots, wondered if they could translate that popularity into a fashion brand.

“I said to Jessica, ‘Hey, why don’t we just make your own line?’ ” Tina says. “ ‘Everything you’re wearing is selling out.’ ”

They knew enough not to manufacture and sell products themselves—it was too expensive and complex. The Simpsons were familiar with licensing through music merchandise, such as tour T-shirts, where they’d lend out Jessica’s name for a fee.

It’s a model best known in the entertainment industry (think Star Wars characters on everything from Legos to watches), but licensing became a vastly bigger business in the 1990s when fashion labels wanted to move into categories they didn’t already dominate.

So while design houses such as Calvin Klein or Ralph Lauren were experts in clothing, when they wanted to expand into eyeglasses or home goods, they would license their name to various manufacturers who’d then make the products and sell them to retailers branded with the designer’s name.

Depending on the arrangement, the brand owner might have a lot of control over the licensed goods—input into design, approval over all finished products—or very little, essentially handing out their name and receiving revenue in return.

It’s not uncommon for brands over time to develop an entire ecosystem of licensees, paying one to produce socks and another to make duvet covers. Licensing allows for low-risk product expansion, but with a smaller return, the deals usually route only 7% to 8% of sales to the owner of the name or brand.

Simpson, at 5 feet 3 inches tall, was known for her soaring heels. After her film debut—as Daisy Duke in the 2005 Dukes of Hazzard movie—“everybody was hyperfocused on the Daisy Duke [jean shorts] and the cowboy boot,” Simpson says. The Simpsons knew their first product line had to be shoes.

In the shoe-licensing world, there was one towering figure: Vince Camuto. The son of a seamstress, Camuto had been in the shoe business for more than 50 years, starting as a shoe repair clerk.

A founder of Nine West in 1978, he eventually hatched the Camuto Group, a powerhouse that had its own lines of shoes, acted as a licensee for other brands, and, eventually with Simpson, licensed out her name to manufacturers making other products.

Although many designers chased the high-end customer who’d pay $700 for Christian Louboutins, Camuto had mastered the stylish, midpriced shoe. Known for translating runway looks into mass-market fashion trends, he’d created commercial juggernauts such as the Tory Burch Reva flat, which sold for a little less than $200.

When the Simpsons first reached out to Camuto, he didn’t know much about Jessica. “Really, his son watched Newlyweds, and he was the one that said, ‘Dad, you need to look at Jessica Simpson, and I think that should be your next licensee,’ ” Simpson says. Camuto ended up with a 25% stake in the Simpson brand, along with the master license.

Their first shoe together was a red high-heeled “Daisy” cowboy boot, a replica of the one she wore in Dukes—and it became an instant hit. “He could pick a bestseller every time,” Tina says. “And they remain our bestsellers,” Jessica adds.

After making a splash with the shoes, they wanted to crack clothing. Camuto’s vision for the Jessica Simpson Collection was approachable clothes with a fashionable edge sold in midrange department stores.

The collection had flashes of Simpson’s signature flair—fabrics with no animal pattern too noisy and high heels that often hovered at 4 inches—but the overall aesthetic was suburban mall clothes, such as fringed jeans and tightly fitting floral dresses.

By 2014, Camuto still produced the shoes in-house, licensing almost 20 more product lines, including perfume and jeans, to other manufacturers.

The brand was steered out of LA under Tina’s direction, with Jessica’s involvement in the business varying depending on what else was going on in her life. Simpson hired close friends, including one of her future bridesmaids and her fifth-grade dance teacher, while ceding the day-to-day to Tina, who divorced Joe in 2013.

“There is a boss, and it’s my mom,” Simpson says. “She’ll be pinching my arm in a meeting if I’m saying the wrong thing.”

Retail executives were impressed with Tina’s work in the nonglamorous parts of the business, such as analyzing sales figures. “It’s not like some licensees where it’s just basically giving a brand to someone and that licensor collects a check,” says Jack Gross, CEO of One Jeanswear Group Inc., a licensee for Simpson’s jeanswear line.

One former designer at a licensee says Tina required written approvals over every style detail, so a minuscule change, such as the finish on a shank—the metal button on a jean’s fly—would mean weeks of holdup as they waited for her sign-off.

“As much as the process bogged us down,” says the designer, who asked to speak anonymously given exit-agreement terms, the business succeeded compared with other celebrity brands “because of Tina.”

Simpson was the brand frontwoman, always up for promoting it, whether in meetings or in-store appearances. The most unusual thing about her was that there was virtually nothing she could do wrong.

A major risk for a celebrity brand is that the celebrity will do something dumb or repugnant—there’s a morality clause in pretty much every licensing contract, industry lawyers say, for things like trashing hotel rooms or ending up in jail—but Simpson’s reality-TV exposure meant she could hardly shock her customer base.

“Quite frankly, Jessica, no matter what she did, even if she said something that some would say would be off-color or different, the consumer never responded negatively, which was an amazing feat,” Gross says.

In less than five years, the Simpson-Camuto team managed to build a booming brand that spanned nearly three-dozen categories. In 2010 the Jessica Simpson Collection brought in $750 million in sales, hitting $1 billion in 2014.

But signs of trouble began to appear around that time. When Tina visited Camuto that fall, his usual high energy seemed flagging, and Tina, who describes Camuto as “a father-mentor type of a businessman to me,” asked him to give her advice about the future of their business as if she were his daughter.

“He’s like, ‘If I was you,’ ” Tina recalls him telling her, “ ‘I’d get a little money on the table for Jessica, because retail is unpredictable.’ ” The Simpsons, still owning 75% of the business, began meeting with potential suitors.

Camuto’s funeral, January 2015: A who’s who of fashion filled the wooden pews of St. Ignatius Loyola church on Park Avenue in New York City.

Garmentos mixed with executives, designers with financiers—the CEOs of Macy’s and Theory; the president of Lord & Taylor; Tory Burch, Steve Madden, and Tina and Jessica Simpson, with Jessica providing a quote for the funeral’s program: “I will forever walk in your shoes … you made them.”

While Camuto was eulogized as a brilliant merchant, some in the crowd studied the Simpsons, who were reeling from Camuto’s death at 78; a private man, he’d never told them he had cancer.

Camuto had built the Jessica Simpson Collection into one of the most successful celebrity-licensing empires in the world—so much so that other Hollywood types had approached him.

“They all want to be another Jessica,” he told a trade publication about a year before his death, but “it would be very difficult to duplicate.”

The Simpsons, too, wondered what they would do next. In the music business, the talent was only as successful as their star producer; for Tina and Jessica, Camuto had been theirs. “Sometimes you get a hit song and sometimes you don’t, and Vince was our hitmaker,” Tina says.

As Camuto steered the Simpson brand to new heights, another model of brand management had gained popularity, shaped by a financier named Robert D’Loren. Historically, apparel brands had only a few paths to survival. If you were considered valuable, you would plan an initial public offering or get scooped up by an apparel conglomerate such as Nike Inc. or VF Corp.

If your brand was distressed, you end up the target of a leveraged buyout by private equity, which would pledge to cut expenses and fund growth—only to bury the company under the weight of its own debt, as happened famously with Limited Stores and Neiman Marcus Group LLC.

In some instances, as with J.Crew Group LLC, a company would briefly go public, only to still be swallowed up by a private equity firm.

D’Loren had worked on Wall Street, where he played around with alternative financial models. He structured the first bonds where the assets were intellectual property, like music or films, helping David Bowie raise $55 million by selling bonds backed by future album royalties.

Later he did the same with apparel trademarks and future licensing revenue. Then, around 2000, he had an idea for a new type of retail business, modeled on entertainment royalties, and deployed it at a company called Iconix Brand Group Inc.

Iconix bought brands for cheap, licensed them out, and drew what revenue it could from them. Like music copyrights, the expectation was that these brands’ cash flow would decline without more investment, and that was fine, as long as Iconix kept acquiring fresh brands.

“Don’t invest anything into supply chain, design, etc., and minimize marketing; just let the income streams naturally fade over time,” D’Loren says. “The key to the model being sustainable” is to keep buying new brands to replace those declining income streams.

That’s exactly what Iconix did, with Bongo, Rampage, London Fog, and other brands. Iconix’s stock soared, and competitors, including an upstart named Sequential Brands, run by Iconix defector William Sweedler, swarmed in.

This new form of brand management company was a collision of the old-world Garment District and Wall Street—businesses often founded generations back by Jewish or Italian immigrant tailors making deals with slick bankers looking to squeeze money out of a brand name.

While at Iconix, Sweedler had encountered a hungry, young operator named Yehuda Shmidman, who joined the company barely out of Yeshiva University, after an entrepreneurial stint selling iPods loaded with oral Talmudic teachings to New York’s Orthodox commuters.

By the time Shmidman was 23, he was Iconix’s director of licensing; within five years, its chief operating officer. Sweedler, chairman of Sequential, recruited him as CEO.

As with just about every licensing pairing, Sweedler and Shmidman were an odd couple. Sweedler, the race-car-driving son of the founder of Joe Boxer (which Iconix had acquired years earlier), lived in Connecticut and summered on Nantucket, whereas Shmidman lived in the Bronx and worked 24/6; you could reach him at any hour of any day, except the Sabbath. For a while their partnership worked.

When Shmidman joined Sequential, the company had made only one recent acquisition, a little-known shoe company. In his first three years as CEO, he closed at least eight deals worth almost $1 billion. Even so, Sequential’s model was still a bottom feeder similar to Iconix’s.

After Simpson approached him, Shmidman saw an opportunity to transform his company into something sexier: Rather than juice what was left of a distressed brand, Shmidman could buy a brand at the top of its game and pump it into a megabrand.

During trips to LA, he pitched the Simpsons—international growth, great partnerships with licensees, a sparkling website, cosmetics, home products—over lunches at Santa Monica’s Ivy at the Shore, a celebrity hot spot known for $44 lobster Cobb salads and paparazzi.

“He had a lot of really amazing ideas,” Simpson says. “I didn’t meet with anybody else that believed in me quite like Vince until Yehuda.”

In April 2015 they closed the deal: Sequential would acquire a 62.5% interest in the Jessica Simpson Collection, for $117 million.

If buying Simpson was a coup for Shmidman’s new strategy, his next deal—for Martha Stewart Living Omnimedia Inc., two months later—was an all-out revolution. At $353 million the acquisition was Sequential’s largest by far.

Wall Street loved the back-to-back Simpson and Stewart deals, ushering Sequential from a third-tier player into the big leagues alongside Iconix and Authentic Brands Group LLC, a growing competitor. People were calling Shmidman the pied piper of brand management.

But it didn’t take long to realize Sequential had gotten ahead of itself. “I looked at the prices they were paying and thought, ‘How in God’s name are they going to make enough money through licensing to cover the costs?’ ” says Michael Stone, chairman and co-founder of brand licensing agency Beanstalk Group LLC. “I couldn’t do the math.”

Neither could D’Loren, who by that point had left Iconix. “When this all started, people didn’t realize what the real model was about,” says D’Loren, who now runs Xcel Brands Inc., the operating and livestreaming company behind Isaac Mizrahi, Halston, and others. The brand licensing model, he explains, was never a retail or wholesale strategy, but a “financial model.”

To digest the acquisitions, Sequential had loaded up on hundreds of millions of dollars in debt, and the blockbuster Stewart deal was dragging down profitability. Stewart, who was paid $6.6 million in 2017 by Sequential, had a board seat and the title of chief creative officer.

She insisted on maintaining her New York headquarters and her team. (Stewart, who owned 10.9% of Sequential stock as of August, declined to comment.) The Simpsons were a small-scale version of the Stewart problem, keeping their several-person brand team and California office.

Despite having backed the generous deal terms and promises months earlier, Sweedler and the board, under pressure to meet ambitious quarterly earnings targets, squeezed Shmidman to cut the businesses’ expenses.

At the time, physical retail—being decimated by e-commerce—still accounted for 92% of Sequential’s sales. But commitments Shmidman had made the Simpsons, such as a significant presence online, were never going to happen.

“It’s hard in this industry to do any investing in the brands,” concedes Rick Platt, who was a division president at Sequential from 2013 to 2016 and now runs the licensing and development company Brand Matter.

“If it’s a public company, you’re targeting 75% or 80% operating margins, and that’s the board’s biggest focus.”

On a Paris shopping trip in early 2017, Tina Simpson got a call from Shmidman: He’d been fired from Sequential. “It was a real shock,” she says. “I was like, ‘Oh, what, wait, what happened? We’re just getting started.’ ” No one else from Sequential bothered to tell them, the Simpsons say, or gave them much guidance on where their brand was headed.

Inside Sequential, Shmidman had lost a power play. Wall Street was spooked by the company’s overloaded debt and its missed earnings targets, and the stock price slid. Shmidman had wanted more money to support expansion, but Sweedler objected; also, sources say, he may have disliked his CEO’s perceived self-promotion, particularly a Wall Street Journal headline calling Shmidman “Martha Stewart’s New Boss.”

In any case, the pied piper of brand management was out. (After Sequential, Shmidman founded his own brand management company, WHP Global, which now owns Anne Klein and Toys ‘R’ Us. He declined to comment on his time at Sequential.)

With Shmidman gone, the Simpsons felt “not protected,” Jessica says, describing themselves as “little ladies yelling, jumping, and trying to get attention in a corporate world.”

They couldn’t even get resources for basic things such as a website, and sales stagnated. “I’m like, ‘Well, where is that percentage of money that you’re getting going? Why is it not going toward my brand growing?’ ” Simpson says.

Simpson knew her customers but says Sequential executives wouldn’t listen, brushing off her suggestions and calling her “irrelevant”—which cut to the core of her insecurities. “I think they wanted to blame me,” she says. “They were making a lot of excuses, and I was the excuse because I didn’t have a movie out.”

By now, Simpson was also struggling with substance abuse problems, which peaked in 2017, including the widely mocked Ellen interview. (She later admitted she’d been drinking beforehand.)

Getting treatment after her subsequent Halloween blackout, she focused on her health, figuring that she didn’t matter to Sequential anyway. “When you’re with a company that doesn’t care or believe in you, it makes you really not want to earn them money,” she says.

Tina was getting tired of waiting around. In 2017, Shmidman’s replacement as CEO had touted that Sequential was building a Jessica Simpson e-commerce site; almost two years later there still wasn’t one.

“I was like, ‘How can we be a brand this big and we don’t have a website? This is crazy.’ So I said, ‘Just give it to me,’ ” Tina says.

She hired a designer who put up a website via Shopify. The move awoke something in Simpson, who started putting products online that retailers didn’t pick up—and they were selling. Tina was left wondering what, exactly, Sequential brought to the table.

“Seeing what we could do with the website, that we did that on our own, made us really realize, more than ever, like, ‘We’ve got to buy this brand back.’ ”

In early 2019, with Simpson giving her approval from the hospital, Tina reached out to Sweedler about a takeover. Jessica says Sweedler “gave us a number,” and the Simpsons put together a financial model and a proposed deal, but Tina says the price kept increasing. (Sweedler declined to comment.)

Sweedler had his eye on a bigger sale. Desperate for cash, Sequential reached a deal in April 2019 to sell the Stewart business for less than half what it had paid, receiving the bargain-basement price in part because of the stink of desperation. Its debt was largely held by a lending arm of KKR & Co., the $450 billion private equity firm.

The whole market knew of Sequential’s dilemma: If it couldn’t pay its debt, KKR wouldn’t hesitate to put it into bankruptcy. “The writing was on the wall, honestly,” Tina says.

Then Covid-19 hit. Although Sequential could continue to try to sell assets to stay afloat, no one was going to bid today for what they could get tomorrow in bankruptcy for a lot cheaper. Sequential cut budgets as it scrambled to find a lender other than KKR to finance it, but no one bit.

This time the Simpsons were going to wait out Sequential’s collapse.

A few years ago, Simpson signed a lucrative book contract about being a billion-dollar boss. But she didn’t write it. (Also, for the record, she was never a billionaire.

At the height of the business, Bloomberg Businessweek estimates, the Simpsons would’ve gotten $13 million or less the year the brand brought in $1 billion in sales. The Simpsons declined to comment on their personal finances.)

Instead, Simpson decided to be candid with her fans, writing about her early sexual abuse, alcohol problems, and her strained relationship with her father in Open Book. The memoir became a No. 1 New York Times bestseller, which, Simpson says, she cried about for five straight hours when she got the news.

For almost her entire career, she’d been told how and who to be: Lose weight, gain weight, sing like this, don’t say that. “I just was like, ‘Oh, wow, people do want to hear my voice,’ ” she says.

With Sequential circling the drain, the obvious next move would be to team up with another brand management company in its place. But Simpson didn’t need a producer anymore; she was ready to be her own producer.

“At the beginning of the business, it was a lot about people-pleasing,” she says. “Then we realized we actually are the leaders.”

In January 2021 the Simpsons hired boutique investment bank Threadstone Capital LLC to arrange financing so they could buy back the Jessica Simpson Collection. “Jessica’s message since I’ve been involved has been very, very clear: ‘I want my name. I want the control of my company.’ She views it very much as part of her identity,” says William Susman, managing director at Threadstone.

The Simpsons weren’t worried that another party might outbid them. Whatever the world had thought of Jessica’s business sense, or Tina’s, for that matter, the duo had made a shrewd move when they signed their initial operating deal with Sequential—inserting a clause that didn’t allow the company to sell the brand from under them without their consent. Sure, another bidder could make an offer, but without the Simpsons’ blessing, it would be pointless.

Sequential filed for bankruptcy in Delaware in August and began selling off its brands. In November a bankruptcy judge approved the Simpsons’ $65 million bid for Sequential’s majority ownership stake, financed largely by the Simpsons themselves with two additional lenders.

The business was supposed to be doing billions in sales by now; instead, its valuation had decreased by almost half since they sold it to Sequential. (Although Tina says the brand was on track to sell $725 million to $750 million in 2021, potential bidders who reviewed the collection’s financials say sales were about $500 million in 2020.

Asked to elaborate on the dramatic uptick, Tina says the brand “experienced tremendous growth coming out of the pandemic.”)

The Simpsons are sketching out plans for life as independent owners. Jessica is now 41; Tina turns 62 this month. They intend to keep all of its 20 or so licensees in more than 30 categories and are expanding into all those areas Sequential never did, plus more: face rollers, yoga mats!

Pet accessories, which Jessica’s 9-year-old daughter is helping design! They’re also thinking about hatching their own licensing company, applying lessons learned from the Sequential years. “We want to build our own IP platform, so that we can sign other people under us, and our umbrella, and we will take good care of them,” Tina says.

But the retail and celebrity moguldom landscape they’re reentering looks radically different from when the Simpson brand was at its peak a decade ago. Chains such as Macy’s and Dillard’s, where the collection sells, are being hammered by online competition. Supply chain disruptions are making it difficult to get products into stores.

And Simpson’s original business model, in which she licenses her name for just a small portion of sales, has been replaced by more lucrative models for celebrities. Simpson says she admires Kim Kardashian, a neighborhood mom friend (it is LA) who holds majority stakes in both of her billion-dollar businesses.

“She reminds me of myself in a lot of ways: She’s very vulnerable, very honest, self-deprecating, and driven,” Simpson says. “I wish I had a little bit more of her confidence.”

Since the sale went through, a whiff of that confidence is starting to surface. On Instagram, where Simpson now has 5.7 million followers, she recently posted, along with a new song she released without a record label, a photo of herself wearing what one might imagine a Jessica Simpson-fashion generator would do to boardroom attire: snug white T-shirt, silver chains, a pile of ponytailed blond hair, and a black bell-bottomed power suit.

“Working on lots of ideas to bring into the line for you: skincare, furniture, or maybe some health and wellness products I’m passionate about,” she wrote to her fans. “What are ya thinkin’ would be exciting to see me creating for y’all?”

In less than 24 hours, there were close to 90,000 likes and no shortage of focus group insight: shorter heels for tall girls, a plus-size line, even a suggestion for Simpson-branded probiotics for gut inflammation. “After 16 years, stepping into that role of ownership of my name and myself,” Simpson says. “It’s about time.”

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