Jason grew up the son of Jeff Van Sickle, who started working as an Intern Architect around the time that Jason was born. Jason's dad would eventually become CEO of GLMV Architects, which is one of the largest architectural firms in Kansas. Jason learned valuable lessons about hard work and dedication from his dad. He also developed a deep sense of compassion from his mom Janice. She was a pediatric nurse and a volunteer at many Wichita nonprofit organizations.
After graduating from college, Jason went to work for Wichita's largest real estate appraisal firm. While working on appraisals, Jason met real estate developer Jack DeBoer (founder of Residence Inn, Summerfield Suites, and Candlewood hotels). Jack had just started his fourth hotel chain, Value Place (rebranded as Woodspring Suites), and Jason was offered a job as the company's first Market Analyst. Within a year he was promoted and tasked with creating a Research & Market Planning Department, which went on to help plan and build over 100 hotels.
In 2008 Jason was contacted by the Director of the Wichita State University Center for Real Estate to help grow the Center's research capabilities. Jason accepted and became the center's first full-time Research Analyst. While at the university, Jason worked evenings and weekends getting development experience by purchasing, remodeling, and reselling houses. In 2010 he expanded into multifamily housing, with the development of his first apartment project. Over the last decade, Jason has developed 363 housing units that include single-family homes, adaptive reuse apartments, urban infill apartments, and suburban apartments.