Little did he know that he'd win the accolade twice, and come runner-up another year just behind one of his comedy inspirations, Tim Vine.
"I would have won it three times if he hadn't turned up that year," Masai joked.
The West Bromwich-born comedian is ecstatic to be bringing home the trophy for the second time, for a pasta-based pun.
Audiences loved: "I tried to steal spaghetti from the shop, but the female guard saw me and I couldn’t get pasta."
And his triumph in 2016 was down to the one-liner: "My dad suggested I register for a donor card – he’s a man after my own heart."
Commenting on his win, Masai said: "It's fantastic, especially to be bringing the trophy back to the Midlands, I'm actually very proud.
"It's been a very busy morning, I was just on the phone to a radio station in New Zealand."
The 41-year-old comedian is also a care worker for young adults with autism, but now works part-time so he can pursue his comedy career.
And humour has always been something that's run in Masai's blood.
The Black Country comic said: "I went to George Salter high school in West Bromwich. I was always the class clown, making everyone laugh. I was always quick-witted.
"And then I started writing jokes as a hobby about 15 years ago. After three years, I saw the Dave's Top 10 Jokes of the Fringe list, and I thought, one day you're gonna get one of my jokes on there.
"So that's what inspired me to start doing comedy, to get a show with the Edinburgh Festival and hope that one day, one of the joke judges would to my show and pick one of my jokes.
"And it's happened twice now!"
Masai was also the runner-up in 2014, with the quip: "I've written a joke about a fat badger, but I couldn't fit it into my set."
He was pipped to the post by one of his comedic inspirations, Tim Vine, whose winning joke was: "I've decided to sell my hoover… well, it was just collecting dust."
However, Masai wasn't bitter, as he was beaten by one of his idols. He said: "Funnily enough, Tim Vine is the man.
"I used to watch Tim Vine videos and think 'that's the type of style of joke writing that I like'.
"When I was younger it was Bob Monkhouse, I enjoy a lot of his stuff, and there's also Gary Delaney who's one of the best joke writers around. So it's mainly the one-liner comedians that are my inspiration."
The 41-year-old is currently giving it everything he's got at the Edinburgh Fringe Festival, performing seven shows a day - split into performances with "clean" jokes and more "adult" jokes.
"I love everything about the Fringe," Masai said. "The people, the audiences, meeting other comics.
"There's a bit of a magic spirit with Edinburgh that I've not noticed anywhere else during festivals. It's the longest-running arts festival in the world so it's a very special place for me."