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Stone’s breakthrough came in the late 19th century when he partnered with fellow Bostonian Charles Hayden to establish Hayden, Stone & Co., a prominent financial brokerage. Together, they diversified their ventures, investing in coal mining, steamship lines, and transportation businesses. Notably, Stone was the president of the Atlantic Gulf & West Indies Steamship Company and helped organize the Eastern Steamship Line in 1900, optimizing freight and passenger transportation along the American coast. His business acumen turned him into a multimillionaire by the early 1900s, allowing him to become a philanthropist and prominent figure in New England’s social circles.