Conversation so far:
How did Herb Jeffries's music career begin?
From Detroit, at the urging of Louis Armstrong, Herb Jeffries moved to Chicago where he performed in various clubs.
What year was when Herb Jeffries moved to Chicago where he performed in various clubs?
Erskine Tate signed the 19-year-old Herb Jefries to a contract with his Orchestra in Chicago. While there Herb was spotted by Earl Hines, who hired him in 1931
What did Herb Jeffries gain with his big break?
Herb Jeffries's break came during the 1933 Chicago World's Fair A Century of Progress International Exposition singing with Earl Hines Orchestra on Hines' national broadcasts live from Grand Terrace Cafe.

Question: Was he with a company?
Self-contained rewrite: Was Herb Jeffries with a company?