McGregor grew up in Hobart, Tasmania, and attended Dominic College and the University of Tasmania, where he spent seven years studying law, philosophy, teaching, physics, with an eye to studying medicine, finally graduating with a combined Bachelor of Arts and Bachelor of Economics degree.

[6] McGregor was a cast member on the RMITV flagship production Studio A[7] until its final season in 2011.

[6] He first performed at the Melbourne International Comedy Festival in 2013, winning Best Newcomer for his show My Soulmate is Out of My League.

[citation needed] He appeared in ABC TV comedy series It's a Date in 2013–2014, followed by The Time of Our Lives (2013), Legally Brown and the first two seasons of Utopia (2014–2015).

[9] His six-part comedy documentary series Luke Warm Sex, a show on sexuality and body image, aired on the ABC from March 2016.