It is a fairly calculated leap, however, as Alaimoana has a number of international performances under his belt and thousands of followers online.
His SeriousLi'i? show includes stories about fatherhood, being a New Zealand born-Samoan, and his love for music is demonstrated with some fine singing and guitar playing.
Alaimoana said stand-up satire was not his first career choice and it was more a case of comedy finding him after a serious injury ended his aspirations as a promising rugby player.
"Rugby was my passion so it was hard but I was always a confident speaker," Alaimoana said.
"I was always the one who got called on to stand up and represent my team or my classes at school so it was a logical transition really."
His comedy career started in New Zealand in 2010, before he moved to Canada with his family in 2011.
Alaimoana said he didn't do much comedy there, although he was named runner-up in the Kokanee 2012 Amateur Comedy Contest in Alberta.
Returning to New Zealand in 2015, Alaimoana started performing on the Wellington comedy circuit and attracted favourable reviews.
Although the comedy is irreverent and sprinkled with profanities, Alaimoana maintains his personal charm throughout his performances.
One reviewer said Alaimoana achieved what Neil Thornton has described as the "holy trinity of comedy", writing that he elicits the "Oh, the groan and the clap simultaneously" from an audience.
Alaimoana recently tested a Whanganui audience while performing with James Nikose at Lucky Bar + Kitchen in August.
"I was supposed to be on the bill with Cori Gonzales-Macuer but Auckland went to level 3 so he couldn't leave.
"It's strange times, and most people are over 2020 already," Alaimoana said.
"I've realised this year that in all this turmoil, I'd like to give back to the comedy community so I'll be using some of the funds from the opera house show to donate to The New Zealand Comedy School in Wellington.
"Hopefully it will help a few struggling people to follow their dreams and take the stress off financially."
Also on the bill are comedians Gabby Anderson, Kajun Brooking and Australian emcee Marty Bright.
"Marty is stuck here due to travel restrictions, which is good for local audiences because he is very funny and so are Gabby and Kajun, who now lives in Whanganui," Alaimoana said.
"Don't be that person that can't join a conversation because you weren't there."
SeriousLi'i? - Friday October 2, 7.30pm, Royal Wanganui Opera House. Adult $35, senior $25, group of six-plus $27, door sales $40.
For a chance to win a double pass just tell us where Li'i Alaimoana was born. Send your answer to liz.wylie@nzme.co.nz by Friday, September 25. For more chances to win visit the Facebook page.