Ever since Hilary was old enough to talk she was trying to start a business.

The businesses started simply enough - neighborhood lemonade stands, painted rocks sold door to door, colored napkins sold to her father - and eventually progressed to legitimate businesses as she matured. She sold Beanie Babies on eBay at age 13, sold handbags made with her sewing machine to friends while in high school and started a handmade jewelry business on Etsy in college. Each business brought a taste of entrepreneurship, skills on varying online platforms, and tangible financial success.

​

After college, life got real.

An internship at Macy's led to a full time employment offer for post graduation, so Hilary packed up her dorm room and moved to the big apple. She tried to keep her Etsy jewelry business going on the side, but the time commitment of a full time job pushed her entrepreneurial ideas to the back burner. While at Macy's she honed her skills in merchandising - working as a planner in the Home department, she worked with buyers and vendors to deliver results. Her Excel skills - already something she enjoyed - advanced as she learned to build inventory management and forecasting tools. After three years at Macy's, the city and the job started to wear on her. She feared her creativity and fire for entrepreneurship were fading, and she didn't know if her passion lied in planning. She also missed her Boston based family. So she gave her notice, packed up a U-Haul, and went back to Boston.

​

Post corporate life led her to her biggest success - and biggest failure.

Hilary planned to take a few months off after her corporate job to travel and relax. After trips to Italy, Greece and Thailand, it was time to start thinking about the next steps. To buy herself some time and keep some income flowing, she went back to one of her favorite entrepreneurial past times - selling on eBay. She started buying trendy and affordable women's clothing from a wholesale website to sell on eBay, using herself as a model for photos. Her first six styles sold and turned into a dozen which turned into two dozen and so on, and she soon started her own standalone women's clothing boutique website separate from eBay, named Hilary Caroline Boutique with the nickname H.C.B. The business grew nationwide with accumulating press and blogger mentions, and word of mouth spread locally as Hilary hosted trunk shows in her living room. She decided she wanted a physical foot print for her online store, and an open space in her neighborhood of Coolidge Corner in Brookline beckoned to her. In Summer of 2014 her store opened, re-branded to H.C.B. or Her Closet Boston. The initial success of the store was thrilling, and in early 2016 she decided she wanted a second store front location, and honed in on the Boston shopping mecca of Newbury Street in downtown Boston. The Newbury store opened in summer 2016, and both stores were re-branded - for the final time! - to Hello Caroline. Unfortunately, the Newbury store was never as successful as Hilary needed it to be to cover the expenses at that location. Sales in Coolidge Corner also waned, as consumer retail patterns shifted and brick-and-mortar stores around the country started to shutter. So in late Spring 2017, Hilary made the difficult decision to close both of her store locations. She will continue to run the Hello Caroline website part time for as long as she continues to enjoy doing it.

​

So what's next?

Armed with ample knowledge and learning experiences from her five years running her online and brick-and-mortar retail business, Hilary is ready for the next adventure. Her stores also led her to discover two new passions: graphic design and interior design. Her interest in graphic design grew as she designed creative materials for the store, and in 2015 she started creating her own graphic patterns and designs for sale on Print-on-Demand sites like Society6 and Spoonflower. Her love for interior design and decor was discovered as she decorated her Newbury Street store to perfection, and the design and decor choices in that store garnered praise from nearly every customer that stepped foot inside. She is looking for her next career that will blend both her creative spirit and her sharp business instinct and analytical skills. Until she finds the next perfect step forward, she will continue working on her graphic design pursuits and offer her knowledge through consulting services for other small business owners.

​

What can I do for you?