Lessons Worth Spreading from Jessica Simpson – Singer to $1B Brand Owner

Jessica Simpson is a musician, actress and an entrepreneur. She began to seek projects outside TV appearances and found herself exceling in retail. From where a great adventure begins!
a Jessica Simpson store with a manager
Courtesy: Jessica Simpson
By | 8 min read

Jessica Simpson Collection founded around 2005, it is a signature lifestyle concept for every-woman and inspired as well as designed in collaboration with Jessica Simpson. The brand offers 31 product categories including footwear, apparel, fragrance, fashion accessories, maternity apparel, girl clothing and a home line.

The brand is supported by strong licensees and has a solid department store distribution through Dillard’s, Macy’s, Belk, Lord & Taylor and Nordstrom, among other independent retailers. Annual retail sales for the brand are approximately 1 billion dollars, reports ‘MarketWatch’ 2020. Above all is its founder Jessica Simpson who has foreseen the limited days of a celebrity to grasp the resources and build a more solid future.

How Jessica Simpson’s Story Shaped Her Business and Lessons Drawn

#1 Mindset Around Wealth

Simpson was not from a wealthy family, in her recent book she shared how they were always struggled in debt and the family have to move a lot. Her dad is a preacher and mom is an aerobic teacher at the church, so money back then was not a part of their experiences. And then one day when she passed a kiosk that have all of these little ornaments hang up with its little name of wishes like Beauty, Wise and so on. Yet she goes for the Wealthy one, keep in mind that it would somehow help her make a lot money and to be fulfilled of what the family had lacked of the whole time, which ornament has been along with Simpson from childhood to adulthood. With the certainty that she will always win, and sooner or later the money will come – therefore the risk taker is born.

After all, how Simpson has soon developed her own believe system around wealth has put on the one point that the entrepreneur always remind woman about. That you should believe that you are truly wealthy and has everything that you desired, and you are capable of massive wealth. Because when we shift our belief from lack into that’s–who–I­–am then everything stars happening for us. We are magnets that attract what we believe. In brief, the first thing you need to transform is nothing far but your own perspective and opinion on yourself!

#2 Continuously Show Up, Especially After Epic Fail

Simpson shared on an iHeart interview, it was about the first Mickey Mouse Club casting where she still in her early days of the career and has to face off many other talented such as Christina Aguilera and Britney Spears. Simpson was having it all together until the final round, when she came to sing but blew it off, the moment where she was so close to victory but cannot make it. The event melted her down while her parents start questioning If this is the right path. However, after the fall teenage Simpson was picked up by herself and again continuous to fight for the next twenty-seven years. And I think this is such a reminder for us, we think that all these stars have it all figuring out for them, with all the record deals and book deals handed to them, but it takes years.

And as of now, there was so many of us who want the quick result, the extremely fast progress, the outcome that others have to fight for, for years. Which is not the “norm”, because you are seeing people as they are right now but forget to really take a look at many different chapters of their experiences. Yet, again the lesson here is to continuously show up regardless of when you fail or all the challenges that comes in your way.

#3 Everyone Starts from The Bottom

It was only herself from the beginning, Simpson does her own hair and makeup, drives herself to different shows. The entrepreneur believes that in any role you are playing, you should not be entitled to do less or have the team members to do everything that you do not want to do. You have to be willing to get in and put your hands in there, and of course so does you team. If you are going to be only in your role and not willing to have your hands dirty when push comes to shove, then it would be hard for yourself and the company to go further. All in all, take out your ego and recognize where you really are, be okay with the status and give all hundred percent in.

#4 Know What are the Gaps in The Market

There was the point when Simpson on the Newlyweds TV show and she was being sent a lot of clothes so she could wear them on TV, yet ended up pushing the sale for all those outfits and brand. And that is when the entrepreneur and her mom start questioning what if they wear their own clothes and have their own products sold to the fans? That was 2004, so Jessica Simpson is the pioneer to be a singer that has her own line of business – a personal brand. She started to look for her gap in the market, and that is when daily-woman came into being. She was very clear of the market she wants to serve, that her line of for the everyday-woman.

Jessica Simpson showroom
Courtesy: Jessica Simpson

She was willing to look outside the box, willing to see where the gap in the market were. She was aware of what her fans wants, and Simpson also reminds entrepreneur of moments when you got into the wheels and keep doing the same things over and over again, forget to take a look at what people actually want from you, take a break and step out to have a look. She doesn’t feel like her mission is to have a fashion line but rather it comes from the want to serve and transform life as well as impact people.

After all, Simpson stressed that if you are also looking for a way to serve any communities, just first look for the gap in the market, and what solutions you can bring to the table!

Simpson’s Collection: How They Are Driving a Successful Brand beyond 2020 

Simpson’s brand has surpassed her name and celebrity status and can now exist fully without her. Jessica had 2 choices with her brand: make it premium-looking, expensive, position it as the top choice on the market for women who desperately need to feel better about themselves and dying to fit in a size 0.

Otherwise go the unpopular way and focus on comfort and empowerment at mid-market pricing. Her branding team must have been fast to point out that her own brand was anything but “premium” and that her best bet was using her relatability and imperfect presence. They clearly made the right choice.

The brilliance of her brand is that she understands it can’t only be about her and people wanting to be her. She’s only an element of the brand – so she made it about the consumer instead.

#1 Clear differentiation

Jessica makes it a point to remind her audience that her products are about comfort, not just fashion. She constantly reminds us about how women love her products because they don’t destroy their feet or hurt their bodies in order for them to look beautiful.

#2 In-depth understanding of the target market

Jessica Simpson ecommerce store homepage
Courtesy: Jessica Simpson

Instead of marketing to a certain demographic as most fashion brands do, Jess chose to market to a worldview. By setting affordable prices, she chose the widest market with the most consumers in it, but still set clear boundaries. She knew they were sick of staring at anorexic models on major fashion magazines and not even being able to afford a sleeve from the dresses they wear. She understood there are masses of women who would never give up their comfort to look like a model, and that’s the market she went after.

#3 Massive focus on research

A 2009 documentary shows how Jessica dedicated a lot of her time to go on a world tour to explore different standards of beauty, which made her understand her target market even better. How much time did you take to do proper research into their behaviors, dreams, desires, setbacks, worldview?

#4 No desire to be a trendsetter

Jessica is in it for the long run – instead of being super fashion-forward, she chooses for her brand to be relatable and affordable. She knows that trends come and go and it’s exhausting and expensive for a brand to constantly chase them. The truth is, you can still be in the spotlight by creating products/services/designs that will appeal to people for a longer time.

#5 Co-creation power

Jessica purposefully chose not to become the skinny version of herself people pushed her to be. By admitting she’s been every size there is, she became extremely relatable and connected to both teenagers and women over 40, who now make up her target market. She even pointed out that choosing not to become anorexic has been great for branding, because when you’re that skinny, not every woman can relate to you. The way she looks right now, is an image the majority of women in the world can relate to.

Jessica Simpson design team
Courtesy: Jessica Simpson

#6 Clear brand enemy.

Every powerful brand has a clearly-identified brand enemy. For Jessica’s brand, that’s impossible beauty standards and anorexic-looking women. She creates fashion for all sizes and that’s accentuated everywhere in her positioning.

#7 Cashing in on perceived flaws

While most people focused on making fun of her when she was pregnant and put on a lot of weight, she used her weight gain as a way to cash in on even more brand loyalty and dollar bills. In fact, Jessica launched a maternity line at the time and that increased her fortune by 100 million in the first year.

#8 Multiple brand extensions

She has over 24 products including shoes, clothes, jewelry, and perfume. One of her motos is that there’s no reason to stick to selling just one thing – what is important is to start with one product, solidify its positioning, and then expand.

The Bottom Lines

Jessica Simpson Collection’s founding story is more than just a business venture, it is Simpson’s life and everything she has lived for. Along the journey to bring up such legacy, there are a lot has been learnt, some are motivating, some are inspiring and some are passed around to cultivate a more insightful She-Owns-It community.

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