I'm fascinated by the recent winning streak of Jeopardy champion James Holzhauer. What's unique about Holzhauer's streak is how quickly he has accumulated money. As of Wednesday morning (when I'm writing this), he had won over $1M in just 14 games (for context, Ken Jennings won $2.52M in 74 games) and has the top seven biggest winning days in Jeopardy history.

Holzhauer accomplished this not just by being very good at trivia or by mastering the buzzer (both very important, certainly). He accomplished it by doing something that no contestant has ever done. For years, the standard approach to Jeopardy was to start with the $200 or $400 clues (the easier ones) in each category and then gradually work your way down the category to the most difficult $1000 or $2000 clues. Holzhauer started with the high money clues, so that by the time he hit the Daily Double, he had more money to bet with … and he went all in each time, doubling already substantial amounts of money with every correct Daily Double answer.

Certainly, Holzhauer's career as a professional sports gambler was an asset in this high-stakes approach. His willingness to risk very large sums of money (and lose it all if he got the Daily Double wrong) enabled him to make the kinds of bets that would allow him to amass huge winnings. But we've seen others willing to do "True Daily Doubles" before. I'm most fascinated by Holzhauer's decision to start with the difficult, higher-value clues, going against decades of conventional wisdom about how the game of Jeopardy should be played.

Think about this: In 30+ years, no contestant has ever tried this approach before (or at least, no contestant that might have wanted to try it has been good enough at the trivia and buzzer components of the game to actually demonstrate this approach successfully). Holzhauer has changed the game. We talk about disruption a lot in tech, but Holzhauer has' disrupted Jeopardy. How many future contestants will look at Holzhauer's massive winnings and start picking from the bottom of the board first? How many will be successful versus finding themselves in the red or at $0 due to incorrect answers or a bad Daily Double? Over time, it will be interesting to analyze the relative success of the those that continue to play Jeopardy the "normal" way versus those that try out Holzhauer's disruptive approach.

Holzhauer's success speaks to the value of changing your point of view and of building teams with differing experiences and points of view. Who on your team has the perspective or imagination to start with the hardest clues at the bottom of the board? How could that impact your organization's success in technology, in security and in digital transformation?

Research has long held that diverse teams are more successful. On a homogeneous team, everyone is likely to start with the clues at the top of the board. That might work for a while (hey, it did for Ken Jennings!), but it only rarely yields outsized success (how many Jeopardy champions can you name besides Ken Jennings?). If your goal is to transform your organization, or the industry, or the world, look for a few people with the gumption to turn the game upside down and start with the $2,000 clues.

And speaking of diverse teams, check out VISION 2019, where some of the brightest minds in digital and physical security from all over the globe will converge in Minneapolis to share their unique perspectives and expert insights.

Sandy Carielli

Sandra Carielli
Sandy Carielli has spent over a dozen years in the cyber security industry, with particular focus on identity, PKI, key management, cryptography and security management. As Director of Security Technologies for Entrust Datacard, Sandy guides the organization’s next generation security and technology strategy. Prior to Entrust Datacard, Sandy was Director of Product Management at RSA, where she was responsible for SecurID and data protection. She has also held positions at @stake and BBN. Sandy has been a speaker at RSA Conference, SOURCE Boston, the NYSE Cyber Risk Board Forum and BSides Boston. She has a Sc.B. in Mathematics from Brown University and an M.B.A. from the MIT Sloan School of Management.