At 20 years old his playing career was cut short when a broken ankle failed to heal correctly.
After leaving Liverpool he was offered a coaching position in Singapore for Woodlands Wellington In May 2005 he completed the Amused Moose standup comedy course run by fellow comedian Logan Murray, then began performing in November 2005.
The day after he finished the course, Brown started plans to set up the now cult weekly Outside the Box Comedy Club at the Fighting Cocks pub in Kingston.
To date guests have included: Jimmy Carr, Frank Skinner, Stephen Merchant, Bill Bailey, Lee Mack, Sean Lock, Russell Brand, Rich Hall, Omid Djalili, Dara Ó Briain, Andy Parsons, Jo Brand, Robin Ince, Tim Vine, Russell Kane, Rhys Darby, Russell Howard, Lenny Henry and most notably Robin Williams.
2007 saw a successful gig with Brown hosting and the bill including Dara Ó Briain, Russell Howard and was headlined by Al Murray.
August 2007 saw a successful Edinburgh festival stint for Brown when playing the white half in a show called The Honky and the Wog.
Paddy Lennox, Tom Craine and Maff shared the night and each showcased half an hour of their best material.