John Ian Scott was born on April 28, 1978, four minutes before his identical twin brother Drew, in Vancouver, British Columbia. He has an older brother, JD, and is the second son of James and Joanne Scott. James had fostered dreams of being a cowboy as he had seen on television, and so emigrated from Scotland to Canada as a teenager. He began working in the film industry as an actor, stuntman, and assistant director until the late 1970s. It was around that time when he decided to focus on raising his family, and they moved to a horse farm in the nearby town of Maple Ridge, British Columbia. James worked as a youth counselor, and Joanne continued her career as a paralegal in downtown Vancouver. On their seventh birthday, their father encouraged the twins to get a job. They looked through the help wanted ads, but ultimately started a business with their mother called JAM (for Jon, Andrew, and Mom) making nylon-wrapped clothes hangers. In interviews, they have related how they would sell them door to door, eventually selling thousands to a woman who sold American paraphernalia in Japan.
The boys' continued job search led them to an ad recruiting child clowns to perform in parades. After completing classes with the local Parks and Recreation Department, they were hired at C$10 a gig, eventually making as much as $100 per hour. John, however, grew tired of making himself up, and began to transition as a performer. As a child, he'd seen a magic show on New Year's Eve that inspired him, and by the age of ten, he was making his own magic props; by 15 he was using a barn as a workshop to create large-scale illusions. He studied the definitive volumes of Tarbell Course in Magic, and sought out professional illusionists David Wilson and Shawn Farquhar, who became mentors and friends. He joined the Vancouver Magic Circle and the International Brotherhood of Magicians, and over the next decade he won several awards, including 3rd Best Stage Performer of the Pacific Coast Association of Magicians at 16.
James would commonly renovate the family properties and, from when they were as young as eight years old, he paid the boys to build and repair fences, decks and barns. Even as children, the twins would often rearrange the furniture in their family home. At 14 years old, John and his father moved to Alberta, where they began building the parents' dream house. He spent his sophomore year there. It is during that period that he took on Jonathan Silver as a stage name, using it privately as well. After his grades began to decline, Jonathan moved back to Maple Ridge to complete high school, returning during school breaks with his family and best friend Pedro to assist in the construction.
The boys attended Thomas Haney Secondary School, and while they both played on the basketball and volleyball teams, Jonathan gravitated more to theater and clubs, where he was president of various committees including student government and the graduation committee. After graduation, the family moved into their newly built home, just as the twins were leaving for Calgary to go to university.
After graduation Scott enrolled at the University of Calgary, majoring in business management. Despite having an interest in going into entertainment, the twins did not want to be "starving artists". After researching the topic, and getting advice from their mother's legal firm, they thought real estate would "ease the financial purgatory of being out-of-work actors". During their first semester in college, using a vendor take-back mortgage, they made a $250 down payment and purchased a seven-bedroom property across the street from their university. They cleaned and repaired it, and sublet the remaining five rooms for a profit of $800 a month. They sold the house a year later making a $50,000 profit. They continued to purchase and "flip" homes at large profit margins by making only modest repairs they completed themselves, sometimes living in the homes they were renovating.