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 as a Market Researcher for Grubb & Ellis | Martens Commercial Group. Within six months, Jason had advanced to co-authoring commercial appraisals with the company's Senior Appraiser. 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 (now Woodspring Suites), and Jason was offered a job as the company's first Market Analyst. Within a year Jason was promoted to Director of Research & Market Planning where he led a large staff that worked on over 100 hotel projects.
In 2006 Jason went into business for himself when he and a friend started flipping houses. In 2009 he expanded into multifamily housing, and has since developed over 350 housing units with a market value of $35 million. Jason has also gotten involved in other businesses, but his approach has always focused on innovation combined with analytical analysis. To reflect that focus, Jason rebranded in 2018 by changing the name of his holding company to Innovalytic (a combination of innovation & analytics).