Henslowe was originally a dyer by trade, and was unusual among theatre managers of the day in never having been an actor. He built the Rose Theatre in Southwark in 1587, presumably as an extension of his earlier financial enterprises, which included starch making and money-lending. His career as a theatre manager appears to have taken off in 1592, when his stepdaughter married Edward Alleyn the actor. Henslowe's primary connection to his theatres was financial and administrative rather than artistic; he took a percentage of the ticket sales, and his account books for 1593-1603 (known as his 'Diary') also record payments for licences, costumes, and to playwrights. His 'Inventory' (of costumes, properties etc.) of 1598 also survives.

Dekker's earliest surviving play is The Shoemaker's Holiday (1600), commissioned by Henslowe for the Rose the previous year. Many other plays by him, largely collaborative, appear in Henslowe's Diary, but the majority are lost. He and Marston took revenge on Jonson for Poetaster with Satiromastix , in 1602. He also wrote the greater part of James I's coronation entry, with Jonson , in 1604.

Born joined Henslowe's Admiral's Men at the Rose following the Isle of Dogs affair in 1597; he appears in Henslowe's Diary on many subsequent occasions. The Admiral's Men were taken into the service of Prince Henry about Christmas 1603, and it was in this capacity that Born appeared in the Magnificent Entertainment (Mar. 1604) as 'Zeal'. He remained a member of the Palsgrave's Men (the successors to Prince Henry 's) until at least 1622, and he was one of the signatories when they leased the Fortune in Oct. 1618. As a writer, he collaborated with Rowley in the completion of Haughey's Judas (1601), and on 22 Nov. 1602 he and Rowley received £4 for additions to Marlowe's Doctor Faustus .