In 1996, owner Robert Hardman fired Goff and hired Henry E. (Hank) Scott, a former New York Times Co. executive, as president of Out Publishing Inc., with the charge to rescue the financially troubled magazine company.

Scott changed Out's LGBT focus, arguing that gay men and lesbians had little in common other than political and legal issues.

[7] Despite editorial changes, Out and Pride still faced financial issues and frequent complaints from freelancers and contract employees.

[8] In February 2019, Women's Wear Daily reported that more than forty contributors wrote an open letter to Pride Media and Oreva Capital, its operating entity, as well as its former editorial management partners Grand Editorial and McCarthy LLC, demanding payment for past work.

[13][14] The New York Post reported Pride Media owed more than $100,000 in unpaid ad commissions to PinkNews, a London-based digital publisher catering to the global LGBT audience.

[15][needs update] In December 2018, Raquel Willis was appointed as executive editor, becoming the first trans woman to take on a leadership position at the publication.

[16] While at Out, Willis won a GLAAD Media Award for Outstanding Magazine Article for "The Trans Obituaries Project".

[25] Out introduced a Reader's Choice Award in 2013 in addition to its editorially curated list of the top 100 honorees.