In 1991, while working as an editor for Pink Triangle Press, he founded The Church-Wellesley Review, Canada's first annual print journal for LGBT creative writing, published as a supplement in Xtra!
[2] In 2009, with Shane McConnell, Round began Proust & Company, a musical-literary evening at Glad Day Bookshop in Toronto to help raise awareness of the world's oldest existing LGBT bookstore.
The event featured a cross-section of Canadian (mostly) LGBT writers and musicians, including poets Maureen Hines, RM Vaughan and Keith Garebian, novelists Elizabeth Ruth, John Miller, Storm Grant, Karen X Tulchinsky, and Zoe Whittall, essayist Michael Rowe, YA author Steven Bereznai, musicians Omel Masalunga, Geri Aniceto, Jamie Thompson and the Urban Flute Project, and others.
He served on the jury for the 2011 Dayne Ogilvie Prize, a literary award for emerging LGBT writers in Canada, selecting Farzana Doctor as that year's winner.
[3] In 2015, with Michael Erickson of Glad Day Bookshop, Round co-founded and co-named the Naked Heart LGBT Festival of Words, which became Canada's most racially diverse literary event.
In addition, he has written about and credited such diverse cultural figures as Glenn Gould, Janis Joplin, John Lennon, Sylvia Plath, James Dean, Joni Mitchell, Tennessee Williams, Vincent van Gogh, Oscar Wilde, F. Scott Fitzgerald, Anton Webern, Marcel Proust, Gabriel Fauré and William Shakespeare with the shaping of his creative vision.
The series, which focuses on gay private investigator Dan Sharp, continued with Pumpkin Eater (2014), The Jade Butterfly (2015) and After the Horses (2015), the latter garnering Round his second Lambda nomination.
It became one of Dundurn's bestselling US titles, bringing Round new accolades from such writers as Joan Barfoot, who, in her IFP review of June 15, 2016, called him one of Dame Agatha's "putative heirs."
The company was in operation for five years and produced, among other works, Round's Right to Privacy Award-winning play, Zebra, about the murder of Toronto librarian Kenneth Zeller in High Park in 1985.