Charron Leeper wasn’t looking for a Side Hustle when she started Perfect Pineapple, a head wrap and hair accessories brand.

It evolved from a need. Leeper had begun wearing her natural curls and was looking for a way to keep them frizz-free while she slept. She opted to use the pineapple method. This entails piling the hair on top, then wrapping the rest of the head with a scarf.

Doing this daily sparked an idea for her. Leeper ended up designing head wraps that weren’t only functional, but fashionable enough to even wear to work.

I would sell them to people at my job. It was a very corporate environment, but I was able to wear my head wrapped because I made it look professional. I helped tear down the stigma that head wraps can’t be professional.

Charron Leeper on Perfect Pineapple’s early days.

Her co-workers would admire her head wraps and ask her where she bought them. She told them she made them. A Side Hustle was born.

“I would sell them to people at my job,” she said. “It was a very corporate environment, but I was able to wear my head wrapped because I made it look professional. I helped tear down the stigma that head wraps can’t be professional.” 

Leeper now is an entrepreneur in her full-time job and also her Side Hustle. She started Perfect Pineapple in 2017. She primarily sells online, but also at popup events and trade shows. She had a shop on Detroit Avenue in Cleveland, near the Lakewood border, until recently when the building changed management.

In 2020, Leeper founded Agency Thirty Three, a creative and marketing agency that specializes in brand development and storytelling. 

Being an entrepreneur comes naturally to Leeper. While in elementary school, she helped her mother make and sell Kente cloth bows. She majored in graphic design in college, but as a new graduate was unable to find employment in her field. She took a retail job at a print shop to pay the bills. It would end up offering an unexpected Side Hustle.

Many of the customers Leeper helped also needed graphic design services.

“I would say to them, ‘I can’t say anything here,’” she said. “I would slip them my card and tell them to call me. That’s how I started to get my first clients.”

Leeper would end up landing that corporate graphic design job for which she had longed. She worked for what she described as an “amazing” global company. But there came the point when she believed it would be better to work full-time for herself. 

Giving up a regular paycheck was a bit scary, but Leeper believed that entrepreneurship was her calling. First, she had to do one thing before striking out on her own.

“I prayed, ‘God, if you want me to do this, I’m trusting you that this will be the last full-time job I work as an employee for the rest of my life,’” she said.  

She freelanced as a graphic designer before starting Agency Thirty Three. Perfect Pineapple remained her Side Hustle. 

Charron Leeper owns Perfect Pineapple, a head wrap and hair accessories brand. Many clients like her products because they are made colorful fabrics. In this photo, Leeper works on one of her products.
Charron Leeper owns Perfect Pineapple, a head wrap and hair accessories brand. Many clients like her products because they are made of colorful fabrics. In this photo, Leeper works on one of her products. Credit: Jeff Haynes / Signal Cleveland

Mistake led to birth of Perfect Pineapple head wraps

Leeper remembers needing a scarf to wrap her hair using the pineapple method. Her grandmother, Eunice Brown, gave her one made of purple satin.

Once Leeper tied a knot so tightly that she couldn’t get it out. Since the ends of the scarf weren’t loose, she began twisting and manipulating the scarf around her head trying to create a head wrap. Some of the results were quite stylish.

“That’s when the light bulb went off,” she said. “This is a really cool design for a wrap. I can wrap this one wrap in so many different ways without untying it.” 

It isn’t surprising that Leeper would see the intersection of function and fashion. She has always had a passion for fashion and had even considered becoming a fashion designer. As a youngster, she won an award for her clothing sketches from a local group of fashion designers. 

“I was inspired by Vera Wang,” she said of the designer known for elegant fashions.

Leeper would later replace the satin scarf with one made of a material with four-way stretch. From the stretchy scarf with a too-tight knot came a design that would serve as a Perfect Pineapple staple. When laid flat, the head wrap resembles an envelope. The design allows for a variety of styles to be formed. Head wraps generally require a certain level of skill to do in order to look good and not fall off the wearer’s head. Several Perfect Pineapple head wraps use a special design feature Leeper created. The styles look complex, but they are fairly easy to wrap.

Fashion and function have earned Perfect Pineapple repeat customers, including Lauren Paul of Orlando, Florida. She likes the broad range of colors, patterns and fabrics and owns several of the head wraps. She said the colors of one of her favorites remind her of a unicorn.

“It has metallic pink and blue cotton candy [hues],” Paul said. “I really enjoy that she does things that are eye-catching and that she plays with color.”

Paul is drawn to Perfect Pineapple for practical reasons as well. She has thick hair and likes how the material gives.

“Her head wraps make it easy for you to cover your whole head without having to sit there for an hour trying to maneuver it around and trying to figure it out,” Paul said. “I love the ease of how you can just kind of throw them on, look cute and go.”

Charron Leeper owns Perfect Pineapple, a head wrap and hair accessories brand. She's shown here at her former shop in Cleveland. The business is now primarily online. She stands in front of colorful boxes filled with inventory.
Charron Leeper owns Perfect Pineapple, a head wrap and hair accessories brand. She’s shown here at her former shop in Cleveland. The business is now primarily online. Credit: Jeff Haynes / Signal Cleveland

Her grandmother was guiding force for Charron Leeper’s Side Hustle

Leeper started Perfect Pineapple in her grandmother’s basement in Oakwood Village. Her grandmother was a trusted sounding board. Leeper enjoyed running head wrap concepts by her grandmother because she knew she would be honest. Brown would ask questions such as, “What’s the functionality?”

Leeper remembers asking her grandmother for feedback regarding a prototype she was tweaking.

“How do you like it?” she asked her grandmother. “She’s like, ‘Well, this material. Not so much. It slips off my head.”

Brown’s feedback was usually incorporated into the revision.

Her grandmother died about the time the business was getting started. The young entrepreneur lost a treasured adviser.

“She only spoke when she really had something to say,” Leeper said. “It was either to give good feedback or to ask a question that she wanted me to find the answer to. She was always pushing me to be curious, to do my research and to try different things.

“I still miss her,” Leeper said. “She just believed in me so much.”

Charron Leeper owns Perfect Pineapple, a head wrap and hair accessories brand. Many clients like her products because they are made colorful fabrics. In this photo, she surveys some of her products.
Charron Leeper owns Perfect Pineapple, a head wrap and hair accessories brand. Many clients like her products because she uses an array of fabrics. In this photo, she surveys some of her products. Credit: Jeff Haynes / Signal Cleveland

Pandemic turned out to be good for business

The pandemic was difficult for many businesses, small and large, but it proved fortuitous for Leeper. 

Perfect Pineapple sales increased. When salons were closed during the lockdown, head wraps offered cover for people who couldn’t get their hair done. The rise in remote work meant many no longer had to adhere to strict office dress codes. This made head wraps a new option for them.

The pandemic also proved a good time to start Agency Thirty Three. Conferences, meetings and other events and activities had moved online.

“They needed design work,” she said. “I got contracted to help businesses create a digital presence.”

During the pandemic, Leeper sent some of her head wraps to Tabitha Brown, the actress, entrepreneur and social media influencer with several million followers. Brown shared the Perfect Pineapple products using Instagram Stories, in which “stories”  disappear after 24 hours. 

“I got like an abundance of sales in one day – about $2,000,” Leeper said. 

For Leeper, being an entrepreneur with two businesses has meant learning how to juggle, prioritize and pivot. For the last year and a half, she has focused on Agency Thirty Three. This doesn’t mean she has forgotten about Perfect Pineapple. In fact, some major developments are in the works.

Leeper said that, as an entrepreneur, she measures success not only in terms of sales and the number of clients. She also takes stock of how much she is innovating and turning setbacks into opportunities.

One setback had haunted her. During Perfect Pineapple’s early days, Leeper had started the process of getting a patent on her twist-and-wrap design feature. Back then, she didn’t have the money to complete the patent process. Without a patent, Leeper said she wasn’t able to stop other brands from incorporating her innovation into their products.

“It was a huge blow,” she said of not having a patent.

But not a crushing one.

“This is my path,” she said of entrepreneurship. “You have to go through those hard spells and just figure it out.”

Leeper said she “just continued to innovate.” A few years ago, she came up with another head wrap design feature she believed could be patented. This time she could pay for the full application process. All she had to worry about was the U.S. Patent and Trademark Office granting her a patent.

Charron Leeper owns Perfect Pineapple, ahead wrap and hair accessories brand. Many clients like her products because they are made of colorful fabrics. She didn't start out intending on a Side Hustle. Making head wraps stemmed from her need to keep her natural curls frizz-free.
Charron Leeper owns Perfect Pineapple, a head wrap and hair accessories brand. She didn’t set out intending to start a Side Hustle. Making head wraps stemmed from her need to keep her natural curls frizz-free. Credit: Jeff Haynes / Signal Cleveland

Bouncing back from a blow

Leeper’s patent lawyer recently telephoned her. 

“Well, they got back to us,” the lawyer said.

Leeper braced herself. The patent process had gone on for a few years. She didn’t quite understand what her lawyer was saying. Was this good news or bad news?

It was great news. Leeper had secured a patent. 

“Oh, wow,” she said when she realized she had gotten the patent.

She was stunned.

“It almost felt like it wasn’t real,” Leeper said. 

Still, she was overjoyed.

“It felt like it was a real victory,” Leeper said. “There was both gratitude and a sense of real accomplishment.”

She said the patent will be used for a head wrap design scheduled to be released in the Fall.

Leeper said having a patent is a game changer. Competitors won’t be able to steal her designs. Having a patent gives her another business advantage.

 “It makes for a better, more confident conversation looking for investors when the product that I’m selling has a type of IP [intellectual property] protection,” she said.

Leeper is preparing to refocus on Perfect Pineapple. New designs and inventory are coming. She hasn’t routinely restocked while most of her attention has been on Agency Thirty Three. Several styles are currently sold out on her website. She’s also deciding whether to keep the business strictly online or look for another storefront. So far, she’s leaning towards keeping it online.

Leeper likes the direction she is going in as an entrepreneur.

“I believe I’m coming into my fruitful season,” she said.

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Economics Reporter (she/her)
Economics is often thought of as a lofty topic, but it shouldn’t be. My goal is to offer a street-level view of economics. My focus is on how the economy affects the lives of Greater Clevelanders. My areas of coverage include jobs, housing, entrepreneurship, unions, wealth inequality and pocketbook issues such as inflation.