The family operated a small town store called The Hub, managed by his brother Sherman and his mother until its closure in 1960.
This necessitated him to attend school only during the morning hours, while working in the afternoon, something permitted by North Carolina law then.
Much like he did during high school, Leon attended nearby Wingate College during the morning so he could manage the factory for the rest of the day.
After a discouraging sales trip to New York, Leon nonetheless persisted and was able to develop a market for his bedspreads in Puerto Rico.
In 1958, Levine, realizing he would have to make a major capital investment in new equipment in order to stay competitive, sold the company.
He liked the simple concept and in November 1959, at age 22, he opened a similar store in the 1500 block of Central Avenue in Charlotte, a place that sold items with a $2 ($21 in 2023 money) maximum price.
In 1974, Family Dollar moved its administrative and warehouse space to a newly built facility in Matthews, North Carolina.
During a summer vacation to Florida in 1957, Levine met Barbara Leven, who lived in Chicago; they married in February 1958.