For Rian Robertson, appearing on Jeopardy! was 15 years in the making. After finally earning his place behind the podium, the Ottawa, Ontario, software developer opened up about the long road to the game show, his family’s reaction and the moment his wife’s excitement became impossible to miss.

Robertson entered his third game on October 5 with $25,901 in two-day winnings after securing two consecutive victories.

A 15-year wait to finally reach ‘Jeopardy!’

Speaking with CTV News on Monday, Robertson described being on the show as “very surreal” after years of trying to make it onto the program.

He estimated that he had been pursuing a spot on Jeopardy! for around 15 years.

The show had been part of his life since childhood. Robertson told Newstalk 580 CFRA that he grew up watching it with his father, making his eventual appearance particularly meaningful.

His most recent audition came in the summer of 2024, following several attempts and different stages of the audition process, including both in-person and online sessions.

After so many years of trying, the call that finally led to the show marked a major moment for the longtime fan.

His wife initially thought it was just another audition

Robertson’s wife, Kristina, did not immediately realize that the phone call was different from the others.

When Robertson was contacted about his availability, he told her, but she initially assumed he had simply received another audition opportunity.

He eventually explained that Jeopardy! only calls contestants about availability when they are looking to bring them to Los Angeles to appear on the show.

That realization quickly changed the mood.

Robertson said both of them — along with everyone else — were excited once they understood what the call meant.

The ‘Jeopardy!’ preparation became his excuse to avoid chores

Robertson said there is no single formula for preparing for Jeopardy!. But once he received the call confirming that he would be on the show, he immediately stepped up his studying.

He described going “into overdrive” with his preparation and even found an unexpected benefit to all that studying: it gave him a reason to get out of doing chores.

The effort paid off as Robertson began his run with consecutive victories. He entered his third game with $25,901 after winning his first two appearances.

His wife’s scream made it into the audience — but not the episode

One of Robertson’s favorite memories came during his second win.

He was the only contestant to provide the correct response at one point in the game when his wife suddenly let out a loud scream from the audience. The reaction was eventually edited out of the broadcast, but Robertson immediately knew where it had come from.

He said her reaction “threw everyone off” and described her as someone who can be loud and emotional.

For Robertson, though, the unexpected outburst only made the moment more thrilling.

A family of six

Robertson and Kristina recently celebrated their anniversary, and the couple have four children together.

He has spoken about having “two older daughters,” both of whom watched his second game with him. Their immediate reaction at the start of the episode was blunt: “Dad, you’re losing.”

Robertson also mentioned having a son during his radio interview. The names and genders of the other children have not been publicly identified in the original report.

From BlackBerry to AI leadership

Away from the Jeopardy! stage, Robertson has built a career in technology.

According to his LinkedIn profile, he is the cofounder and head of AI and relationship intelligence at Bloks, where he has worked since 2017 and held several different positions.

His previous employers include BlackBerry, Cavendish Farms, Visual8 Corporation and TD Bank.

After spending roughly 15 years trying to get onto Jeopardy!, Robertson finally turned that longtime ambition into reality — and quickly became a returning champion with two wins and $25,901 heading into his third game.

Jeopardy! airs weekdays. Check local listings for times, with episodes available to stream the following day on Hulu and Peacock.