Strauss was active in Kuhn Loeb until 1941, although he resented restrictions imposed on investment banking by regulators in the Roosevelt administration and derived less enjoyment from the business. Nonetheless in his role as an investment banker Strauss had become vastly wealthy, and given his humble original circumstances he has been considered a self-made millionaire and a Horatio Alger tale. As one historian has written, Strauss's business success was the residue of "luck, pluck, hard work, and good contacts". Strauss's biographer reaches a similar conclusion: "Strauss reached the top because of his ability, ambition, choices of the right firm and the right wife, and the good luck to start out at a prosperous time." Due to his lack of higher education, Strauss has also been characterized as an autodidact.