He's also been spotted sporting a tutu, fairy wings and a wand.
Every year Glenn has a personal goal to raise at least, get this, $10,000 for a charity. Plus, he hopes to smash that record this year as he throws his fundraising weight firmly behind his friend Mal Law and the High-Five-0 challenge for mental health.
Mal and his friends like Glenn are running a mountain marathon a day for 50 consecutive days to raise funds and awareness for the Mental Health Foundation.
"Life is hard and we all struggle to keep the right balance. I have a blended family with four children, a high pressure job, seven years of family court dramas and costs," Aucklander Glenn says.
"I know how important it is to focus on keeping a healthy mind and the more I looked into the Mental Health Foundation and the proactive work they do, the happier I was to get in behind the cause," he says.
"Mental health is something we all need to be mindful of which is a big reason I chose to get in behind Mal and the challenge."
Glenn met Mal a few years back while traipsing the Waitakere ranges during long training sessions for trail running, where they found a strong connection and are great mates today.
But for Glenn, running with Mal is about more than just mental health and fundraising.
It's also about Glenn's brother Hamish, who was killed in a car crash in 2014. Hamish was one of the most positive people on the planet and Glenn's involvement in a challenge like the High-Five-0 is a tribute to Hamish's audacity and his love of mountains.
So, not satisfied to simply run a few marathons with his mates, Glenn has also organised a charity auction on the evening of the last day of the High-Five-0.
"I try and keep the asking for donations from friends to a minimum and would much rather put some extra time and effort into creating events such as the upcoming auction at College Rifles."
Glenn reckons it's important to have more options for donations than simply giving money. Through an auction, people are getting something back – a great night out and purchasing something awesome that helps out an amazing charity.
"So why not create something where everyone wins!"
To purchase tickets or to donate auction items, call Gina at College Rifles, 09 600 6280 or email firstname.lastname@example.org