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 now 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 graduation, Jason went to work for Wichita's largest commercial 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. He eventually went on to build and lead the company's Research & Market Planning Department.
In 2006 Jason went into business for himself, when he started flipping houses. He also accepted a position with the Wichita State University Center for Real Estate, where he served as the Center's housing research analyst. In 2009 he expanded his business into multifamily housing development, which became his primary focus. To date, Jason has developed over 350 housing units, with a market value of $35 million.