Rick Hendrick, founder and chairman of Hendrick Automotive Group, built the largest privately held automotive dealership group in the United States through scale, discipline, and an intense focus on customer experience. Starting with a single dealership in North Carolina in the 1970s, Hendrick expanded into a nationwide network selling millions of vehicles annually across major brands. He is also a dominant figure in motorsports as owner of Hendrick Motorsports, one of NASCAR’s most successful teams, with multiple championships and a roster of elite drivers. Hendrick’s influence spans both retail automotive operations and the business of American racing.

Michael Jordan, global sports icon and billionaire entrepreneur, transformed athletic excellence into one of the most powerful personal brands in history. Widely regarded as the greatest basketball player of all time, Jordan won six NBA championships with the Chicago Bulls and later parlayed his competitive legacy into business dominance through the Air Jordan brand, a cornerstone of Nike’s empire. Beyond sports, he became a pioneering team owner with the Charlotte Hornets and built a diversified portfolio spanning endorsements, private investments, and philanthropy. Jordan’s post-career success set a new standard for athlete-entrepreneurs, redefining how greatness compounds far beyond the arena.

John W. Henry, billionaire investor and principal owner of the Boston Red Sox and Liverpool FC, built his fortune as a pioneering commodities trader before reshaping the global sports industry through Fenway Sports Group. After founding the quantitative hedge fund J.W. Henry & Co., he acquired the Red Sox in 2002 and led the team to multiple World Series championships, breaking the “Curse of the Bambino.” Expanding his sports empire internationally, Henry later bought Liverpool FC, guiding the Premier League club to Champions League and English title victories. Known for his data-driven, value-focused leadership, he has become one of the most influential owners in modern professional sports.

James “Jim” France, chairman and CEO of NASCAR, is a central figure in American motorsports and a key steward of the France family racing empire. The younger son of NASCAR founder Bill France Sr., he helped expand the organization’s commercial footprint through decades of leadership roles, including as co-founder of the International Motor Sports Association (IMSA). Taking the helm of NASCAR in 2018, France has overseen major media deals, modernization efforts, and renewed focus on long-term growth, solidifying his reputation as a steady, influential force guiding the future of professional stock car racing.

Conor McGregor is an Irish professional mixed martial artist and boxer, known for his charismatic personality, sharp wit, and powerful left hand. He has achieved immense success in the UFC, becoming the first fighter to hold titles in two weight classes simultaneously. Beyond sports, McGregor has established himself as an entrepreneur with ventures in the whiskey industry, fashion, and more.

Floyd Mayweather Jr. is an American former professional boxer and current boxing promoter. Widely regarded as one of the greatest boxers of all time, he has won fifteen major world titles and retired with an undefeated record of 50-0. Mayweather is also known for his flamboyant lifestyle and significant earnings, which have made him one of the wealthiest athletes in the world.

John Menard, Jr. is the founder of Menards, a Midwest home improvement chain. Known for his low-profile demeanor, Menard has built a retail empire, making him one of the wealthiest individuals in the United States.