Life
Henslowe developed extensive business interests, including dying, starch-making, pawn-broking, money lending and trading in goat-skins. He owned property in East Grinstead and Buxted, Sussex, where his brother in law Ralph Hogge lived. Between 1576 and 1586 Henslowe was involved in the trade in timber from Ashdown Forest. However, his main activity was as a landlord in Southwark. One of his authors, Henry Chettle, described him as being unscrupulously harsh with his poor tenants, even though Henslowe made many loans to Chettle and they seem to have been on friendly terms.

Business Interests
In 1584 Henslowe purchased a property known as The Little Rose, in Southwark, which contained rose gardens and, almost certainly, a brothel. In 1587, Henslowe and John Cholmley built The Rose, the third of the large, permanent playhouses in London, and the first in Bankside. From 1591, Henslowe partnered with the Admiral's Men after that company split with The Theatre's James Burbage over the division of receipts. Edward Alleyn, the Admiral's' lead actor, married Henslowe's stepdaughter Joan in 1592, and they worked in partnership.
In 1598, Burbage's company (by then, the Lord Chamberlain's Men) erected the new Globe Theatre in Bankside; Henslowe moved the Admiral's Men to the north-western corner of the city, into a venue he had financed, the Fortune Theatre. John Taylor, the "Water Poet", petitioned the King on behalf of the Watermen's Company, because of the expected loss of business transporting theatre patrons across the Thames.
He also had interests in the Newington Butts Theatre and The Swan.

Theatrical Interests
Henslowe and Alleyn also operated the Paris Garden, a venue for baitings; early in James's reign, they purchased the office of Keeper of the Royal Game, namely bulls, bears and mastiffs. In 1614, he and Jacob Meade built the Hope Theatre in Bankside; designed with a moveable stage for both plays and animal baiting, it was the last of the large open-roof theatres built before 1642. The animal-shows ended up ascendant at this venue. The induction to Ben Jonson's Bartholomew Fair, performed at the Hope in 1614, complains that the theater is "as dirty as Smithfield, and as stinking every whit." The theater did not have a regular theatrical tenant after 1617; Henslowe's share in it was willed to Alleyn.

Henslowe's Diary
The papers first came to critical attention in 1780, when Edmond Malone requested them from the Dulwich library; the papers had been misplaced and were not recovered until 1790. Malone made a transcript of the parts he viewed as relevant to his variorum edition of Shakespeare; the original was returned to Dulwich after Malone's death. (Malone's transcript was returned to the library around 1900.) The next scholar to examine the manuscripts was John Payne Collier who inserted forgeries which supported his own theories about Shakespeare.