If all of this seems a bit squirm-inducing, watching a well-meaning, hard-working businessperson hand over the reins and reputation of his company to a comedian for the sake of an eight-minute gag, well, that's the point.
"There are very specific situations that people can be put in that reveal things about their personalities in a very short moment," Fielder says. "When people are on camera or just going through their life, it's in a controlled state of how they choose to present themselves to the world."
"My favorite moments are when they can't put that mask on because the situation is so different," he says.
Those situations -- like convincing a sweet old diner owner to market her business as the only restaurant with bathrooms "not" for customers only -- can come off as mean, a charge which Fielder adamantly denies.
"'Mean' and 'difficult to watch' are two different things," he says. "A lot of people get uncomfortable watching difficult social situations. My aunt can't watch the show. She gets so uncomfortable she has to leave the room."
Not only is his show not mean, he says, it is actually nicer than most reality shows.
Reality shows typically prey on their participants, he says, forcing people to be mean, or more often portraying them as stupid.
"We focus on people you wouldn't normally see on reality shows. The nice sweet people. Sometimes [reality shows] will bring out the nastiness in people, I like to bring out the kindness in people.… [Most reality shows] joke that people are stupid."
The essence of Fielder's sense of humor, he says, is all part of a lifelong struggle to "figure out my personality."
Fielder says he was a shy kid growing up. He learned magic, and worked birthday parties in high school, all in an effort to break out of his shell.
The only son of two Canadian civil servants, Fielder really does have a business degree from a leading Canadian university, a point he makes on the show and when pitching the program to real business owners.
After college he began doing standup and making short videos he would post to the Internet. Those videos landed him a spot on "This Hour Has 22 Minutes," Canada's answer to the "Daily Show," in which he honed his talking-to-real-people shtick.
That Fielder started his career on the internet might not come as a surprise to those who only know Fielder from the internet.
In addition to his television program, he has pioneered making comedy on Twitter beyond the obvious 140-character one-liner.
Fielder nearly broke the internet last month, when he asked his mostly college-aged Twitter following to text their parents "got 2 grams for $40," a reference to buying drugs. Then immediately text them again with "Sorry ignore that txt. Not for you."
His followers, thousands of them, then took pictures of the text message exchanges parents had with their kids, believing they had stumbled on a drug deal.
"Say goodbye to college," wrote back one mother, clearly not amused.
In a similar prank Fielder had kids ask their parents if Dollar Store condoms were any good.
The internet pranks stem from the same impetus as the television show, finding the humor in putting real people in familiar but otherwise uncomfortable situations.
Fielder says he is preparing the show's second season. Already he has in mind a bit in which a mattress store lets people stay overnight in order to field test their sleeping experience.
But for now, he's going for a walk.