Jeopardy! champ imparts winning business strategies

Ken Jennings opened the 20th annual BenefitsPRO Broker Expo by sharing winning tips to apply to any endeavor.

BenefitsPRO Editor-in-Chief Paul Wilson (left) shares audience questions with Ken Jennings, whose keynote address on Mon., Apr. 29, 2024, marked the beginning of the 20th annual BenefitsPRO Broker Expo at the Gaylord Rockies Resort & Convention Center in Colorado. (Credit: Lauren Lindley Photography for BenefitsPRO)

As an American kid growing up overseas, Ken Jennings devoured episodes of Jeopardy! — not just because it was one of the few English-language TV shows he could tune in every day after school. The young book-lover also relished the parade of contestants, “who seemed to know everything.”

“As a nerdy kid who liked to read, it was like watching a superhero movie,” Jennings recalled during his opening keynote address on Monday, April 29, 2024, at the 20th annual BenefitsPRO Broker Expo held this year at the Gaylord Rockies Resort & Convention Center in Colorado. “It was very formative for me, and it really changed my life.”

Jennings, 49, now boasts such unusual accomplishments as being the Jeopardy! contestant who won more money than any other; who racked up the longest winning streak in the show’s 40-season history; and who followed in the footsteps of popular longtime Jeopardy! host Alex Trebek. His BenefitsPRO Broker Expo keynote speech was aptly titled, “Adapt to Win.”

Over a lifetime of studying game shows, Jennings said he learned that winning contestants share three key characteristics: They passionately prepare, they quickly adapt to change, and they’re always curious.

“The more things change,” Jennings said with a friendly, relaxed demeanor, “preparation is the one thing you can rely on.”

“I was lucky enough to watch Alex Trebek for 20 years,” said Ken Jennings, the triumphant Jeopardy! contestant who now serves as the show’s host despite lacking previous broadcasting experience. “The business analogy is, watch other people who are great at their craft” when you hope to succeed at that same endeavor. (Credit: Lauren Lindley Photography for BenefitsPRO)

Consider how Jennings prepared 20 years ago for his first Jeopardy! appearance. In the run up to the show, he made a habit of positioning himself opposite the television in his home during nightly episodes. He’d stand behind a waist-high recliner to emulate the podium where contestants stand during the show, and used a Fisher Price clicking toy in place of the actual Jeopardy! buzzer.

“I felt like a moron,” Jennings said. “But the funny thing is, when I got to the show, and I was standing behind the podium, I thought, ‘This is about the height of my recliner at home! And when I picked up the buzzer, I was like, ‘This is like that Fisher Price toy… I just remember that great feeling of thinking maybe, just maybe, I’m the most prepared person in this room right now.”

The experience of mastering Jeopardy! also reflects the many years of watching TV after school as a kid, when all Jennings wanted was to be able to exhibit the kind of subject-matter mastery that he observed on the gameshow. But to presume such winning contestants are some sort of superhuman savants, he said, is to lose the battle before its even begun.

“I’ve now met hundreds of [contestants],” he said, “and they’re just like everybody else. The only difference is, they’re curious about everything, and they pay attention to everything.”

Developing eclectic interests was Jennings’ top success tip.

“When you’re interested in something, you don’t have to try to study it. It just sticks in your head… So the secret is, love everything. Because if you’re open to everything [and] curious about everything, facts just stick.”

See also:

Let new business come to you: 10 add-on sales strategies for benefits pros

4 tips to drive agency success through accountability

Tips and strategies for successful mentorship