[1][2] In 2017, Louisville Business First honored him with the Excellence in Leadership Award for his successful NuLu redevelopment in the East Market District and current efforts in the Portland neighborhood.
Holland moved to New York City in the early 1990s, and after a brief stint at October Films, worked for three years at Unifrance.
He has owned The Group Entertainment since 2005, an independent film production company, which formerly included a talent management business.
The label features Ben Sollee, Nerves Junior, Cheyenne Marie Mize,[11] The Old Ceremony,[12] and Irish singer-songwriter Mark Geary, whose 2004 release Ghosts featuring backing vocals by Josh Ritter and Glen Hansard approached gold status and received critical acclaim in Ireland and the United States.
Holland also worked with Jack Harlow on his 2020 EP Sweet Action, whose single "What's Poppin" reached the top 10 on the Billboard Hot 100.
[13][14] This renovation of a historic building opened in the fall of 2008 in the area that he dubbed "NuLu" in the East Market District.
By 2020, his Portland Investment Initiative had spent over six years and $35 million constructing new residences and renovating warehouses dating back to the 19th and 20th centuries.