Having worked in a large, successful white insurance firm, Gillespie saw the need to bring better insurance services to Chicago’s black community and founded Liberty Life in 1919. Unlike other insurance firms, Liberty Life was the first to offer whole life insurance, rather than industrial policies, capitalizing on the growing prosperity of the city’s black families. Though it took several years to collect enough funds to manage all of the firm’s expenses, by 1925 Liberty Life had admitted assets of $495,000 and over $8 million of insurance in force.