Looking at Katy Huguenard's family history, one common thread spans three generations: real estate. Her grandfather, father, uncle, and brother have all been involved in the commercial property sector, making entrepreneurship a prevailing presence in her life.

Raised in the North Shore, after graduating from Miami of Ohio, she was drawn back to Chicagoland with an offer to help start an unknown tech company. As one of their first employees, Hugue...