Dai studied Theatre and Film at Victoria University of Wellington, before winning 'Best New Face' on TV2's Pulp Comedy in 1999, the Billy T Award in 2002 and the Fred Award in 2007. In 2004 and 2005, he toured the shows The Hot Stepper and Champagne Table Tennis, and performed at the Tokyo Comedy Store and in Melbourne and around Britain. He has performed at the New Zealand International Comedy Festival and in 2008 he was invited to the Montreal Just For Laughs Festival and recorded for a televised Gala special.

Dai spent a period on TV3's Sunrise morning show as the gadget guy, and subsequently featured on C4 hosting Insert Video Here and a comedy travel show Roll The Dai. He has recorded two DVDs titled Dai Another Day, released in 2009 and Adapt or Dai in 2013.