Growing up in Te Kuiti, music was Regan's escape.
His mother had walked out and his father left Regan and his three brothers "to raise ourselves".
By the time he was 13, Regan had discovered that music was his passion.
He might have failed school and "everything to do with education" but he was
taught to play the guitar by patched gang members and found music was a great equaliser.
He played his first gig at the age of 13 at the Te Anga Tavern. Two people were killed at the pub that night, he said.
And although his past might sound chequered, it was just normality for Regan.
Despite what was going on around him, he kept his nose clean and his focus clear.
"I was just there for the music and [to] get out of there."
The musician, now 33, escaped the King Country and moved to Australia when he was 19.
Now back living in Mount Maunganui, the musician has been tagged as the Bay's rising star.
He's about to release his second album, has an internationally renowned producer behind him and a growing following in Japan.
But with a beanie pulled low over his forehead, the soft-spoken father-of-one still comes across as a shy boy from Te Kuiti.
He describes his music as "acoustic-based Kiwi music".
"I can't really liken it to something else. The lyrics are kind of like, you say whatever you want to say.
"It's more like punk in the lyrics but the sound is quite soft. It's like soft punk, reggae, jazz-blues mix, if that's such a thing.
"I reckon it's just Te Kuiti music."
Regan was happy, originally, just to have his music heard in his home town, but one of his brothers sent a demo to a music industry bigwig.
The recording fell into the hands of Mike Nielsen, who produced British band Jamiroquai.
"All of a sudden there was a guy who found and produced Jamiroquai helping me record."
The result was Regan's debut album, Wiser, which was released last November.
The album's songs have been played on Kiwi FM, George FM, BOP FM and Classic Hits.
"It's kind of weird; it's kind of underground but commercial at the same time.
"It has a good appeal."
His growing success has come after two decades of hard work.
In Australia, he "played flamenco music with gypsies", as well as playing in a reggae band.
And six years ago, he made his first trip to Japan, a country which has fascinated him since childhood.
"I have been chipping away at it for awhile, totally self-funded.
"I started out [in Japan] sleeping in the park and ended up sleeping in the Ritz Carlton.
"It took me three years."
But Regan is not really a Ritz Carlton kind of guy - "I hated it" - and prefers more modest accommodation when he travels to Japan these days.
His partner, Kaori, is Japanese and the couple have a 10-month-old son, Maui.
Next year, the musician - who prefers to be known only by his first name - will embark on a four-month tour of Japan.
His debut album is to be released there by Tower Records - the biggest distributor in Japan.
And he is already booked for the Fuji Rock Festival - Japan's largest outdoor music festival.
After that, he plans to make his first trip to Europe and tour Britain.
But his New Zealand fans won't be neglected - Regan is planning a national tour this November.
His lyrics reflect his view on life.
"It's just about things that have been happening to me, like sleeping in the park.
"Rich people, poor people, knowing that people are just people."
And the birth of his son inspired a new set of lyrics for his second album, which is just weeks away from being finished.
"[Being a dad] turns you into a grown-up.
"[Maui is] awesome, there's heaps of good energy."
Before moving to Mount Maunganui, the keen surfer lived at Raglan.
But he always had a strong connection to the Bay - his grandparents lived at the Mount and he has fond memories of holidays at the beach.
He loves the local community, which is why he is taking part in LoveTheMount Sunday Sessions at Satori Lounge.
Regan takes to the stage on September 12.
He can also be seen opening for Tahuna Breaks at the Colosseum on September 24 and for the Black Seeds at Brewers Bar on October 22.
Hard work paves way
Growing up in Te Kuiti, music was Regan's escape.
His mother had walked out and his father left Regan and his three brothers "to raise ourselves".
By the time he was 13, Regan had discovered that music was his passion.
He might have failed school and "everything to do with education" but he was
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