Her life had a less-than-auspicious start, however. The youngest of three children, she struggled to overcome a speech impediment. Her family also wrestled with financial challenges. After high school, Orman went to the University of Illinois at Urbana-Champaign. There she majored in social work, but left in 1973 before completing her degree. Buying a van, Orman set out to see America with some friends. She ended up in Berkeley, California, where she eventually landed a waitressing job at the Buttercup Bakery. During her seven years at the bakery, Orman pursued a dream of opening up her own restaurant. She shared her dream with one of her longtime customers, Fred Hasbrook, and he gave her a check for $2,000 in 1980. Hasbrook also approached other customers to contribute to Orman, and she ended up with $50,000 for her restaurant venture.
Knowing little about money management or investing, Orman sought help from a representative at Merrill Lynch. She met with a broker, and put her money into an account there. Although she had told him that she only made $400 a week and needed to keep her money safe, the broker chose to pursue the risky strategy of buying options. He told that she could make "a quick $100 a week" and had her sign a blank form giving him control over her funds. The plan worked well at first, but she ended up losing all of her money within three months.
Meanwhile, Orman had been trying to learn as much about investing as she could. She read the Wall Street Journal and Barron's, and she tuned in to the PBS financial series Wall Street Week. After losing all her money, Orman decided to become a broker and applied to the same Merrill Lynch office where she had lost her earlier investment.
The company hired her "to fill their women's quota," Orman explained to Publisher's Weekly. She was told that women weren't meant to work this business and that she would be gone in six months.
During her training, Orman discovered that her broker had violated the company's policies. She sued the company, and Merrill Lynch eventually settled with her out of court. Orman studied hard to learn about all sorts of investing opportunities, and she did well for her customers. In 1983, she left to join another firm as a vice president. Orman started her own firm in 1987.
Orman got her first media exposure through a local radio station after writing to complain about another guest that provided incorrect information on an investment product. "The next Saturday I went down there and did a show. After that, my phone started to ring off the hook," Orman told Success magazine. Soon Orman became a guest expert for other radio and television programs.