Dai Henwood on Life, Laughter, and Growth

From “class clown” to Officer of the NZ Order of Merit, Dai Henwood opens up about the real work behind making people laugh: curiosity, grit, and character.

He traces the spark from Wellington College to Victoria University, the moment he realized he was a comedian, and the work ethic he learned watching his parents. We dive into people skills as a superpower, saying yes to scary opportunities, and the women who’ve backed him at every step.

Dai also shares his candid philosophy while living with stage-four cancer—why he waited two years to go public, how to feel emotions rather than outrun them, and the mantra that keeps him grounded: “Optimism won’t cure me, but pessimism will kill me.”

Above accolades and TV gigs, Dai’s proudest achievement is the person he’s become as a husband and father—proof that success is who you are, not what you have.

It’s truly a gift to share this episode with Dai Henwood on The Guest Speaker.