You probably have heard about a young man named James Holzhauer who snagged his 22nd Jeopardy win last Friday. Just as the excitement was building, it’s that time of year when Jeopardy will be taking up contests among special contestants.  It’s the Jeopardy Teacher’s Tournament time, so, Holzhauer will be on a “Jeopardy vacation” the next couple weeks. Chances are the time-out will allow time more suspense to build. Any story on Holzhauer’s struggle has a longer time frame.

Ken Jennings

Holzhauer’s quest to become the leading Jeopardy contestant has a long way to go–Ken Jennings was finally edged off the show after 74 appearances. In fact, it’s almost too early to be talking about beating Jennings only there is one thing that makes Holzhauer’s quest more noteworthy: His style of play. Holzhauer is a professional gambler and he bets big and accumulates money much faster than Jennings did. Some fans grew tired of Jennings slow methodical approach to winning (perhaps like more Jeopardy winners).  Holzhauer’s appearances have been more exciting according to those who like his gambling nature.

Jeopardy is obviously a very well run show and a great international brand. Jeopardy has past winners on tournament of champion shows so over the years fans are able to see the best of the best.  Sometimes the greatest champions go head to head, so there will be a time when Holzhauer will likely go head to head with Jennings.  But for now, the pressure builds and the streak may just continue for some time.

Success, Celebrity and Wealth

If you look at the most financially successful people, I don’t think it’s any surprise that such success is often cloaked in a kind of celebrity. Such celebrity can be connected to sports. A highly successful entrepreneur may decide to invest in a soccer team; buy a baseball or football franchise; or own a stable of great race horses. And sometimes it works in the opposite direction, a great athlete will accumulate more by making great business investments. Many wealthy celebrities are also drawn to the movies or the world of music.

But regardless of how much celebrities today mix their career with music, movies, and sports–the top 2% are still the top 2%. What took a rare level of talent and even a rarer amount of commitment sometimes looks easy. That’s deceptive. James Holzhauer and Ken Jennings have tremendous talents, but they didn’t acquire their knowledge from osmosis. Each week when they are on a winning streak they defeat a number of excellent opponents.

When I was younger, I knew several people with great talent and intelligence. But often they weren’t interested in success as we know it. They set their sights on a more manageable livelihood. It was then that I found out National Merit Scholars sometimes become auto mechanics. superb athletes sometimes want work with high school kids rather than work through the rat races for the gifted.

Entrepreneurs Are Different

An entrepreneur works never-ending hours in the early days and often has a vision that seems to decry logic, but is potent. The entrepreneur keeps after his or her vision while others would have cashed in. The superstar super-entrepreneur athlete has a hall of fame career, but a personal drive signals that  he or she is not even half way home. Some have bigger appetites than others. We live in a supersized time. Financial success is some times talked about in $Billions not $Millions.


Mixing sports celebrity, business success and the movies was Joe DiMaggio. A cultural icon who is unknown to many today.  As a sports fan I know that perhaps the greatest career record that may never be broken is Joe DiMaggio’s 56 game consecutive hitting streak [Sporting Chance Press author, J. D. Thorne covered the steak in our book The 10 Commandments of Baseball: An Affectionate Look at Joe McCarthy’s Principles for Success in Baseball (and Life)]. The streak was watched closely all over the country and provided a kind of media respite from the early World War II years in Europe (soon to involve the United States).  DiMaggio was a steady kind of Ken Jennings player who was an excellent fielder, hit home runs and batted at a high average. He was also an athlete who was intense and suffered through stress. Each day as the streak went on, the nation checked the newspapers and listened to the radio for the latest contest between DiMaggio and the opposing pitchers. Sometimes a hit came late in the game to keep the streak going. Often, DiMaggio’s Yankee teammates would do whatever they could to help the streak going. Other Yankees put their egos on hold and cheered DiMaggio along.

DiMaggio persevered.  On July 17, 1941 the steak ended at 56.

Later DiMaggio married movie star Marilynn Monroe.

DiMaggio started in the pros in 1936 and his career was split in half by the 3 years he served in the military after his streak year in 1941.  He came back and played through 1951.  DiMaggio was one of those players who would command many millions of dollars if playing today. After his baseball career, DiMaggio in his late 40s was persuaded to become the Mr. Coffee spokesman in 1972. His quiet sales pitch sold well to Americans at that time.