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Jessica Simpson's Billion-Dollar Secret: 'Being Underestimated Is a Superpower' Building a fashion empire has taught the pop star that when people assume you're clueless, it only gives you more time to prove them wrong.

By Frances Dodds

entrepreneur daily

This story appears in the March 2022 issue of Entrepreneur. Subscribe »

Image Credit: Art Streiber

"Ringing the bell was a wild experience, I have to say."

Jessica Simpson is sitting in her company's Los Angeles office on a cold January afternoon, near a small mountain of shoeboxes emblazoned with her name. "Everyone was, like, this is amazing! This is amazing! People were really digging it for me, and I was, like, "OK, guys … I'm going to ring the bell now..."

Simpson lifts a hand into the air, long green nails curled around the imaginary gavel at the New York Stock Exchange.

"Ding! I don't know what I just did." She widens her eyes and turns her head from side to side, consulting invisible onlookers. "Wait, does this mean I have to run Wall Street now?"

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She does a big Texas cackle, deep from the diaphragm, sliding up a few octaves at the end. After 20 years in the spotlight, Simpson, 41, has mastered this particular note: laughing at herself, playing a little dumb for your enjoyment. But if, by now, you still think the pop singer (turned reality star, turned actress, turned fashion mogul) is clueless, well, then — you have a thing or two to learn about the perks of making yourself the punchline. Simpson knows that when your audience is laughing at you, they're distracted. And that gives you time to size them up.

"Being underestimated is the superpower," Simpson says. "It makes you want to soar over everyone. But really, it's better to do it patiently. I play along in a way that I let people know I'm playing along."

And Simpson's long game has paid off. Today her most enduring and lucrative venture is the Jessica Simpson Collection, a clothing and lifestyle brand that first cleared $1 billion in annual sales in 2012. But even this journey has been riddled with lost time and underestimation. From the start, she did not have complete ownership; she and her mom Tina cofounded the business in 2005 with the shoe titan Vince Camuto, and later sold a majority share to the public company Sequential Brands (which earned Simpson her starring role at the stock exchange). But Sequential was an unsteady owner. "For a good three and a half, four years, every time we visited the Sequential offices, I told our team, "Guys, we're on the Titanic, and we're circling the iceberg!'" Tina says. In November of last year, after Sequential declared bankruptcy, the Simpson women finally took control: They paid $65 million to buy back their brand in full.

"I think back to when we were starting out and we were super young and naive," Tina, 62, says. "People thought, "Oh, those silly women. We can pull the wool over their eyes. You know, it's Jessica Simpson and her mother!' It's pretty funny when you think about it."

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Like mother, like daughter: Tina and Jessica get a kick out of being underestimated. They've discovered there's power in flying under the radar, in reading the room when no one thinks you're paying attention, in speaking up even when you're not sure you're right, in stockpiling knowledge for the moment you're ready to say, This is what we're going to do.

"So many men in suits have made me feel underestimated, at this point I just have to laugh, like, "Oh, you need a hug,'" Simpson says. "I can't even think of one moment in particular because it's happened my whole career. I was always the little girl who had to come in and sit with men in suits, you know? But now I get to wear the suit."

Image Credit: Art Streiber

The idea for the Jessica Simpson Collection first came to Tina in 2003, when Jessica was on Newlyweds: Nick & Jessica. The hit MTV reality series documented the beginning of Simpson's short-lived marriage to Nick Lachey, resident heartthrob of the boy band 98 Degrees. At that point, Simpson had put out three albums with hits like "Irresistable," "With You," "I Think I'm in Love with You," and "I Wanna Love You Forever," but Jessica's dad and manager at the time, Joe Simpson, didn't like that the record label was branding Jessica as a sex kitten. A former Baptist minister, he thought fans would see a more down-to-earth side of her at home, farting in sweatpants (this happened a lot). It worked. Newlyweds got Simpson noticed in a whole new way — in large part for the gaffes she was prone to making on camera. Curled on the couch, picking at a bowl of tuna from a Chicken of the Sea can, 23-year-old Simpson asked, "Is this chicken that I have, or is this fish?" Lachey turned to her in confused horror, and the moment was cemented in pop culture memory.

In her 2020 memoir, Open Book, a No. 1 New York Times best seller, Simpson wrote: "I know there are people who think I can't string two thoughts together … In the beginning of my career, somehow, I was always the joke. Everybody made fun of something I'd say, and I admit, I definitely played into it. People's laughter meant a lot to me, and being the joke validated me being smart to myself. It felt like I could pull one over on somebody.
I thought, How dumb are you to think I'm that stupid?"

Simpson's "blonde moments" always seemed authentic, but also like there might be a split-second calculation between the moment something popped into her head and the instant it came out of her mouth. She clearly enjoyed watching the shock waves of a ditzy comment ripple outward. "I do like catching people off guard," Simpson says. "That is one thing about me. I know how to say something that will drop a jaw."

Simpson was funny and relatable, and everything she wore on Newlyweds sold out. "I said to Jessica, "It's great that we're doing this for everybody else,'" Tina recalls. ""But what if we do it for ourselves?'" Tina had always been entrepreneurial, running the numbers at her grandparents' gift shop in Texas when she was a kid, and when Jessica and her younger sister, Ashlee, were growing up, teaching step aerobics at church. (Her class was called "Heavenly Bodies.") Once Jessica started performing, Tina designed all of her outfits and costumes, working with seamstresses to sew looks from scratch. But the Simpsons thought it made sense to license Jessica's name to an already established manufacturer. So they reached out to Vince Camuto, the shoe designer who cofounded Nine West and the multibrand conglomerate Camuto Group.

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Jeff Howald is now the CFO of the Jessica Simpson Collection, but back in 2005, he was CFO of the Camuto Group. He remembers Camuto's decision to pay $15 million for the Jessica Simpson Collection master license. "I think he saw younger versions of himself in Tina and Jessica," Howald says. "Newlyweds gave this impression that Jessica was kind of the dumb blonde, but he saw a very intelligent businessperson in her. Vince had an eye for the smallest of details, and that's how Jessica and Tina are. Tina is in every product meeting, and Jessica is in many, giving feedback to the licensees. A lot of celebrities want to sign up and let everybody else do the work, but Tina and Jessica really work the brand."

From the beginning, Tina says, "We knew we wanted it to be affordable. We never wanted to be in Neiman's or Bergdorf's or anywhere like that. We wanted to hit the midtier because those are her fans. Those were the people coming to see her shows and buying her records. And Jessica's personal style and the way she dresses are really pretty happy. It's approachable and attainable."

Simpson's line was sold in mall department stores like Macy's and Dillard's, where she already spent a lot of time. "There's not much to do on tour," she says. "So I would go to the mall and shop. I liked seeing how people dressed. I'm very observant, and I would totally be that person sitting on the bench staring at everyone. I get why my grandparents did it — it's fun! You can get a sense of what people are shopping for, what they're needing."

The Collection has always been a balancing act between what Jessica would personally wear and the trends her customers are buying. "There was a time when these tall heels and platforms went away in the marketplace," Tina says. "But Jessica was, like, "That's what I like to wear. Keep doing the Dany — our big platform heel that's been going forever — which Jessica can literally wear to the beach. So she wanted to take the risk and stick with it, and now the platform trend is back and it's been a great year for us because we always made them so people know to come to us."

On the other side of the equation, one of the brand's all-time top-selling shoes is a ballet flat called the Mandalaye, which Cynthia Nixon's character Miranda wore on an episode of And Just Like That…, the Sex and the City reboot. "Jessica would never personally wear that shoe," Tina says, "but we know there are people who would, so we took a risk on it."

Jessica and Tina say many of their risks come down to instinct. "For my mom and I, intuition is everything," Simpson says. "Like, if we're not feeling it in our gut, you didn't feed us dinner."

And certain things that didn't feel quite right in the first place didn't turn out as they hoped.

In 2015, Vince Camuto died unexpectedly, after a quiet battle with cancer. "He didn't let anyone know he was sick, not even his closest employees like myself," Howald says. "One of my first calls was to Jessica. She was so shocked, in tears, it was like her own father had died."

In the year before his death, Camuto had given Tina some advice. He said the retail landscape was changing, so it might make sense to sell some of the brand while they were ahead.

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"He said to take some chips off the table," Jessica says. "I don't know that he really meant as many as we did." She laughs. "We were, like, chips off the table, cool, OK!"

But when the final agreement with Sequential came through, Tina says, "I'll be honest with you. I wasn't happy with the 62.5%, and the people negotiating that deal for us knew it. But our lawyer put in a very strong operating agreement that gave Jessica 175 pages of rights. I wouldn't have signed it without that because even if they owned 62.5%, when it came to the product — the look and the feel — we got final approval. In my daily life, I don't think of myself as a control freak, but when it comes to Jessica's brand, I am. I wanted to protect her."

Image Credit: Art Streiber

There is a term that Simpson uses often in her memoir, Open Book, to describe painful moments of vulnerability: "nekkid." "Not naked, nekkid. Truly bare." And she's had a lot of those moments. For years, as a child, Simpson was sexually abused by a family friend's daughter. When she finally told a friend about this, the friend spread cruel lies about Simpson around their middle school, and Simpson was ostracized. At 13, she was a finalist for The All New Mickey Mouse Club, along with Justin Timberlake, Ryan Gosling, Christina Aguilera, and Britney Spears. But before her final audition, Simpson made the mistake of watching Aguilera's audition on the backstage monitor. When Simpson got out onstage, she froze. She lost the spot and didn't get signed to Columbia Records for another four years. That was only the first time she was ranked against Spears and Aguilera — a recurrence throughout her career. Turning off her inner critic was often exhausting. Before she aced her breakout role in The Dukes of Hazzard, she'd heard the director was resistant to casting her. "I think he thought I was too dumb to play a character as strong and smart as Daisy Duke," she wrote in Open Book. And when John Mayer broke up with her before she performed at a Dolly Parton tribute, she had a whiskey-abetted meltdown mid-"9 to 5," telling the audience: "This song is too good for me."

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Many aspects of Simpson's life settled into place once she met her second husband, the former NFL football player Eric Johnson — with whom she now has three children. But other things fell apart. As she prepared to give birth to her oldest daughter, Maxwell, her dad came to see her in the hospital and broke the news that he was leaving her mom after 34 years of marriage. He said it was she, Jessica, who had inspired him to do this when she walked away from her first marriage. For Simpson, her parents breaking up was world-shattering. By 2017, she was drinking vodka and flavored Perrier from "glittercups" at 7 a.m. before taking her kids to school, drowning out the pain and anxiety she felt. After browning out at a Halloween party, while dressed up as her friend and "spirit animal" Willie Nelson, she realized something had to change. "When I stopped drinking, it was because I had stopped hearing the voice I really trusted, and I was lost without her," she says.

During the last four-plus years, Simpson has been learning to hear that voice again. But some of those early traumas still haunt her. In moments of extreme pressure or conflict, she often finds herself paralyzed. "Any audition, you name it, I'll blow it," she says. "It's a weird pressure that I freeze under, and it's all these words in my head. I'm like, Ahh! I put a lot of pressure on myself, so I expect other people to hold me to a higher standard."

This kind of brain-wipe panic is a logical part of being underestimated. Proving yourself to doubters means living up to your own expectations, and those are often the hardest to meet. But Simpson has developed strategies to cope with the dreaded "freeze."

"When I have a really important meeting or audition or performance, I try to just meet the stage or the audition or the fashion where it's at in that moment," she says. "Be present. People are always forward-thinking, and it's good to have goals and dreams. But being in the moment and checking out your surroundings—noticing what is around you — that's so important to growth."

According to her mom and Howald, one of Simpson's defining characteristics is how tuned in she is to her surroundings — even when it appears that she's not. "We'll be sitting in a board meeting and I'll think she's not listening to anything because she seems really checked out," Tina says. "But then all of a sudden, she'll come out with the most brilliant question that's been asked all day. I've always thought her mind processes things differently from other people."

Howald mentions this as well. "When we're in the middle of a big meeting with lots of people," he says, "out of the blue, Jessica will ask a very good financial question or suggest a specific solution, like, wouldn't it be better if we handled that deal this way?"

Simpson says that when she seems spaced out, it's often because she's evaluating what everyone is saying — holding their opinions up to the light, wondering why they specifically would think this or that, and how other people in the room might be perceiving the information. "I hear everything. I know four conversations going on around me right now," she says, gesturing to the open office behind her. "I'm always thinking about the person who is delivering the information and the people at the reception area or in the back. I'm very conscious of my surroundings. Even if I'm in the middle of something really chaotic, I can be still. I'm quiet until I'm not."

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But also, unsurprisingly, when a thought is spinning through her mind, and she's not sure other people will think it's smart, Simpson is a huge believer in just saying it. There is a concept of a boss, a very masculine idea, that assumes a leader should always project confidence. Simpson doesn't have time for that.

"Being comfortable with saying something you're not completely confident about is important," she says. "Just because you're not confident doesn't mean it's not an amazing, bright idea. I always advise people to be very open and let it all out because some of the weirdest ideas are the ones that stick."

Image Credit: Art Streiber

Naturally, now that the Simpson ladies are running the business on their own, questions arise. In the office, burrowing into the neck of her chunky sweater, Jessica says, "Literally it was so cold in here today, I was, like, "Mom, did you pay the electricity bill?'" This cracks her up. "No, no, all the plumbing and electricity are good."

After utility bills, one of the Collection's first orders of business is continuing to build out its e-commerce offerings. Back in 2015, Sequential had promised the Simpsons a top-notch website, but it never materialized. Tina got so tired of waiting that she took it into her own hands (and then paid Sequential royalties on the profits from the site it never helped her build). "Everybody told us it would take at least five years for us to see any type of profit from the site, but we had profit in year two," Tina says. "So that was one of those "aha' moments. Like, OK, we can do this ourselves."

For Tina, reclaiming ownership of the Collection has been a kind of coming home. "It's fulfilling the destiny I didn't realize existed when I was younger," she says. "You know, I started over. I got divorced. And it was, like, well, crap, if he was going to leave me, why didn't he do it when I was, you know … younger and hotter?" She laughs, a hearty laugh that almost fills the void of injustice. "But with the business, it's, like, hey, we did all that. So to me, the brand represents that you're never too old, and it's never too late."

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Jessica is not one for regrets, but when asked if there were any "uh-oh" moments in the brand's journey, she thinks of that morning at the New York Stock Exchange, after the sale to Sequential. "I just feel like ringing that bell put a lot of expectation on my name and my brand to be this moneymaker," she says.

Simpson has never liked high-stakes, high-pressure situations. But she's also come to realize that just because a moment is high stakes doesn't mean it has to be high-pressure.

"Being underestimated … it's like a shield," she says. When people overlook and undervalue you, they're leaving you to "prep yourself for the future you want." She continues: "Don't put too much pressure on yourself because it's never make-or-break, you know? There's always a way to make that break. Let time move a little slower so you learn and grow along the way. Then, by the time you get there, you'll be ready."

Frances Dodds

Entrepreneur Staff

Deputy Editor of Entrepreneur

Frances Dodds is Entrepreneur magazine's deputy editor. Before that she was features director for, and a senior editor at DuJour magazine. She's written for Longreads, New York Magazine, Architectural Digest, Us Weekly, Coveteur and more.

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