Long before Shoeaholics existed, Jillan Aimable was already developing her entrepreneurial instincts. As a student, she saved money by walking home instead of taking a taxi, using those savings to buy and resell phones. That habit of spotting opportunities followed her into adulthood. She began travelling to the United States to buy Bath and Body Works products, perfumes, and GNC supplements to sell wholesale to stores back home. She built a small catalogue and personally pitched store owners, gaining valuable experience in sales and business along the way.

In 2009, Jillan was working as an assistant manager of business development at Scotiabank when a trip to Los Angeles changed the direction of her career. She had travelled with her sister in the hope of helping her open a boutique. During the trip, Jillan found herself lost in LA's famous Shoe District. By the time she finally found her way out, she had spent most of her vacation budget on shoes. What began as an unexpected detour quickly became an obsession and sparked the idea for a business of her own.

Not long after returning home, Jillan turned that passion into action and opened Shoe Fetish at Arima Dial Mall in 2010. A year later, the store was rebranded as Shoeaholics. That unexpected adventure in Los Angeles had become the starting point for a business built around helping women discover footwear that suits their style, expresses their personality, and makes them feel confident.

From its first location, the business grew to a second store in Chaguanas and eventually expanded across Trinidad and Tobago. The journey brought its share of challenges, including financial hurdles that led Jillan to secure her first business loan through the National Entrepreneurship Development Company Limited. She also faced the experience of being underestimated as a woman running a retail business. Rather than allowing those assumptions to hold her back, she used them as motivation to challenge expectations through her work. She wants her daughter, nieces, and the women she works with to know that "women can do anything."

One of the most difficult periods in Shoeaholics' history came during the COVID-19 pandemic, when Jillan lost her mother, the person she was closest to in life. Alongside this profound personal loss, the changing retail landscape forced the business to close a few branches and rethink how it operated. Since then, Shoeaholics has continued adapting to challenges ranging from foreign exchange constraints on imported inventory to shipping delays at the Port of Spain. Strong relationships with suppliers and brokers have helped the business keep stock moving and continue serving its customers.

Today, Shoeaholics employs about 30 women, some of whom have been part of the business since its early days. Jillan's ambitions extend beyond the stores the brand has established in Trinidad and Tobago. She hopes to expand across the Caribbean and eventually take Shoeaholics global through online sales, making it easier for more customers to discover their next favourite pair.