At the same time that Carnegie climbs up the corporate ladder of the Pennsylvania Railroad, he learns the potentials of investing money through his mentor and boss, Tom Scott. In 1856, Scott proposes that Carnegie invest in the Adams Express Company, and offers Carnegie $600 to purchase stock. Though Carnegie had never previously considered investing, he is thrilled to receive a $10 dividend check from the investment, and senses a “new world” of moneymaking possibilities (46). Carnegie is particularly excited by the prospect of earning money without working, and begins to eagerly invest his money, quickly amassing a fortune. Carnegie becomes a particularly “shrewd” investor due to his ability to pick stocks with little risk, eventually out-earning Scott, who ultimately goes bankrupt through poor investment choices (48).

One of Carnegie’s core investments is in the Woodruff Sleeping Car Company, which creates sleeping cars outfitted with beds for overnight train travel. Carnegie partners with Scott and John Edgar Thomson to invest in the company. Thomson and Scott create a partnership between Woodruff and the Pennsylvania Railroad, ensuring business for the sleeping cars, and Carnegie agrees to invest the money for one-eighth of the company. Though Carnegie has to obtain the initial payment money through a bank loan, the investment’s dividends “pay off the entire balance” within a year, and it continues to create income for Carnegie for years to come (50).