Ashlee Kennedy
Owner, Hillside Gardens

Ashlee Kennedy is a Colorado Springs native who began her career in the nonprofit world, work that carried her around the globe and gave her a lasting curiosity about other people. A later turn into wine and spirits, where she earned her WSET certification and worked as a spirits rep, put her in front of countless small business owners and planted the idea of building something of her own. At the end of 2021 she and her brother Donavan acquired Hillside Gardens and Event Center, reviving a fading local landmark into one of the city’s favorite gathering places, with a garden center, a coffee shop, a tequila bar, weddings, and a summer concert series that fills the gardens every Wednesday. Her drive runs personal, too. Losing her younger sister in high school taught her early that life is short, and she has spent it making places where her community comes together.