Herb Chambers, self-made billionaire and founder of The Herb Chambers Companies, built one of the largest and most successful auto dealership groups in the United States. Starting with a single Cadillac store in 1985, he expanded into a network of more than 30 dealerships across New England, representing top luxury and premium brands such as Mercedes-Benz, Porsche, and Rolls-Royce. Known for his relentless focus on customer service and sales innovation, Chambers turned a struggling dealership into a multibillion-dollar enterprise, cementing his reputation as one of America’s top automotive entrepreneurs.

Craig McCaw is an American telecom visionary who transformed his family’s cable-TV company into McCaw Cellular, pioneering U.S. mobile networks in the 1980s. After selling the business to AT&T in 1994 for over $11 billion, he went on to build Nextel, Clearwire, and other wireless ventures—shaping modern cell-phone infrastructure. A Stanford graduate and dyslexia survivor, he continues investing through Eagle River Inc. and supports environmental, education, and tech philanthropy.

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.