Herbert Wertheim, optometrist, inventor, and investor, built his fortune through a mix of innovation in vision care and shrewd long-term investing. Founder of Brain Power Inc., he developed tints and protective coatings for eyeglass lenses that became widely adopted in the optical industry. Beyond his business, Wertheim amassed a multibillion-dollar portfolio by investing early in companies like Apple, Microsoft, and Intel, often reinvesting dividends over decades. A noted philanthropist, he has pledged much of his wealth to education, science, and medical research, cementing his legacy as both a pioneer and a benefactor.

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.