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Stories of inspiration from Smart Girl Stories across the globe. Green Roost: Raised In A Family Of Entrepreneurs

Green Roost: Raised In A Family Of Entrepreneurs

Entrepreneurship in the retail world wasn’t exactly Kelsey Settle’s initial plan, but fate had other ideas. Raised in a family of entrepreneurs, she was steeped in the culture of business ownership from a young age.

In her teenage years, Kelsey’s dreams centered around becoming a chef. With a passion for cooking and all things culinary, she imagined herself thriving in the kitchen. Yet, reality hit hard when she experienced the intensity of commercial kitchen life, swiftly rerouting her aspirations.

Unbeknownst to her, Kelsey was already on a different trajectory. Her journey began in a small-town boutique at 16, followed by stints at various retail outlets, including her aunt’s gift shop and even a gig as a “road rep,” peddling retail gifts along the East Coast.

Life Took An Entrepreneurs Turn

Life took a pivotal turn when her aunt, Sharon Clark, extended an offer for Kelsey to manage her new shop, Green Nest, back in Virginia. Initially planning to stay for just a year, fate had other plans. Eighteen months later, Kelsey found herself at a crossroads when her aunt proposed she take over the shop permanently and join the family of entrepreneurs! After much soul-searching, she embraced the challenge, diving headfirst into the world of entrepreneurship.

August 1, 2011, marked the official transition as Kelsey assumed ownership of what would become Green Roost. However, her initiation into business ownership came with a baptism by fire. Just 23 days in, an earthquake rattled Culpeper, shattering her shop’s windows, and testing her resolve. Yet, she emerged stronger, learning firsthand the resilience required in the face of adversity.

Fun Fact: That earthquake was where Kelsey met her now husband, Chris, who was the police officer assigned to her as an escort when her shop had to be secured that night.

The next big hurdle in business came in the form of a cease-and-desist letter. The name of the shop caused a trademark infringement, which forced a rebranding from Green Nest to Green Roost. Despite the setback, Kelsey pivoted her marketing strategy, demonstrating her adaptability and determination to thrive.

A Crash Course In Resilience

Those initial weeks of business ownership were a crash course in resilience. Kelsey quickly realized that flexibility and evolution were essential for survival, lessons that would serve her well through even greater challenges, including the tumultuous events of 2020.

The silver-lining of the shutdown of 2020 was the creation of Green Roost’s online presence. At the very beginning of the shop’s 8-week closure, Kelsey began to develop an online shop and through a self-taught method (aka Google and YouTube tutorials), she launched the first version of This move single-handedly saved the shop during that season and has since become a valuable portion of the Green Roost revenue stream.

The next big pivot in Kelsey’s success came in April of 2022, when she made the investment in a business coach. Through that coach (Emily Grey) and later her mastermind program, Kelsey has found a new sense of passion for entrepreneurship. Joining this community of women entrepreneurs, has allowed her to refocus her business goals and map out her next steps in scaling Green Roost and launching her next business venture, Retail Rituals.

With over 15 years of expertise under her belt, Kelsey has honed a remarkable talent for forging genuine connections with her customers. Through her engaging “Roost Insider” emails, she has cultivated a devoted following, transforming patrons into friends. This unique bond has been the cornerstone of her enduring success, fostering a loyal customer base that steadfastly supports her ventures, year after year.

Growth And Transformation

Like a phoenix rising from the ashes, Kelsey’s journey exemplifies how obstacles can pave the way for growth and transformation. Through it all, she’s emerged stronger, her story a testament to the power of perseverance and the triumph of the human spirit. As Kelsey continues to chart her course in the world of retail, her story serves as a reminder that with determination, resilience, and a touch of entrepreneurial spirit, anything is possible. It is a tale for all entrepreneurs!

Read more powerful stories on our Inspiration page, and don’t forget to follow us on Instagram!

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