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LADY BOSS: Joleesa Holdipp of Klassiq Kidz



Joleesa Holdipp of Klassiq Kidz

Welcome to Lady Boss, SheHub’s editorial collaboration with the Bermuda Economic Development Corporation (BEDC). For the next six months we will feature one female entrepreneur who is making a name for herself on the island.This month, we are launching with Joleesa Holdipp, owner of Klassiq Kidz, which sells children’s apparel and accessories.

In late 2014, Klassiq Kidz started as a pop-up shop on weekends and holidays while Joleesa worked in corporate Bermuda. A few short months later, she decided to take the full leap into entrepreneurship and opened up a store on Court Street in March 2015.

Joleesa tells SheHub that she never had a goal to be self-employed: “Unlike most entrepreneurs, I did not have any huge dream or desire back then, to become an entrepreneur. It was never something I even thought of until I started selling kids’ clothing on the side. To have an actual store was never in my plans. My mom always talked about having one, but instead she pushed me to pursue my dreams instead.”

If one does not understand the amount of time and energy that must be invested in order for entrepreneurs to keep their heads above water, often they think being self-employed is a walk in the park.
Not so, says Joleesa. It’s anything but.

“One of the biggest misconceptions is thinking that someone who is self-employed has unlimited freedom to do what they want. If I had a dollar for every time a person said to me, ‘You work for yourself? You’re lucky! I probably wouldn’t even have to work anymore!
“Yes, I do make most of the rules, I can wear what I want and I may not have to sit at a desk from 9-5 but I am also responsible for everything else. The social media posting, accounting, inventory, also along with everything else that goes on in the actual store, while caring for my daughter. So basically, I never knock off. I’ve worked the hardest in the last four and a half years than I ever worked when I had a 9-5. You have to be willing to put in the work because unfortunately we don’t know the secret to success. We work hard for it!”

And like many female entrepreneurs, who often have to balance home and work life, Joleesa says there are times when she wanted to throw in the towel.

“I can’t say it’s been a smooth ride. There have been hurdles along the way, but I pray every day that I stay motivated and encouraged. I will not succumb to my failures but will keep pressing on instead.”
The mother of one says she loves when she has the opportunity to interact with other female entrepreneurs as it motivates her to be the best that she can be: “I love to be around, chat and converse with other likeminded individuals.”

She cites Rickeisha Burgess, Hanifah Smith and Stacy Hill amongst the many veteran entrepreneurs who she admires.

In 2017, Joleesa was the recipient of the BEDC’s People’s Choice Award for Small business, a recognition she says she did not expect.

“I was surprised! Each of recipients were able to see votes and it was a very close finish between my business and a few others.”

Communication and Development Director of the BEDC, Jamillah Lodge, offers her accolades: “Joleesa being recognised by the people, at BEDC’s 1st Annual Small Business Awards, is a testament to the service she provides to her customers. The People’s Choice can be the most coveted of all awards, because it is the public that votes for you. She was well deserving of the award and we wish her continued success.

Joleesa Holdipp accepts her People’s Choice Awards *Photo courtesy of BEDC

“She also launched the Kidpreneur Extravaganza in 2018 which was a vendor market for young entrepreneurs. It was great to see young people as young as six years old being entrepreneurs. This speaks to Joleesa’s desire to pay it forward in true entrepreneurial spirit. BEDC is looking forward to continuing to sponsor this event which will be held on November 30th this year.”

Like other small business owners, Joleesa is always developing new ideas to keep her business in the forefront of her customers old and new. One of her concepts, the Girl Box.
She explains what it is: “It is a quarterly fun box put together with love by Klassiq Kidz filled with girly items suitable for girls aged five through 14. The Girl Boxes are surprise boxes so you do not know what will be in them until they’re opened. The girls LOVE Girl Boxes and usually want one every time I put a new one together.”

Interested in a girl box for your loved one? They can be ordered online on
Joleesa offers this advice to any female aspiring to become an entrepreneur: “Take the risk and believe in yourself—something that I still write down and tell myself daily.”

Klassiq Kidz is located on 57 Court Street. Follow them on Facebook (Klassiq Kidz) and Instagram (Klassiqkidz & Girlbox_bda).

Are you interested in becoming an entrepreneur? Visit the Bermuda Economic Development Corporation, which is located at 48 Church Street, Hamilton, Bermuda or visit

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