"If things go wrong, your life is at risk and you're really aware of it. The wild is pretty severe, it's a tough world. Things are forever going wrong, and you've just got to deal with it."
"You've got to work with the elements. People assume you turn the tap on and the water comes out. You start to realise it's not like that. You're in charge of all that here."
Last month marked his 20-year anniversary as a real-life renegade - and despite his enduring survival on one of Australia's toughest landscapes, it's surprising to discover that it's human interaction that interrupts his peace.
"You get people who are not used to danger and they may react, things can get ugly very quickly," Glasheen tells news.com.au from his island home.
"Men can be worse. I've had men crying in boats wanting to turn back. I'm saying, 'no we have to keep going, the island is up this way, we have to keep going. There's nowhere to go back to'.
"You start to realise you're a bit vulnerable, but you've got to do things rationally here. You have to learn to be calm and think, but it's not easy when people are getting emotional around you, when you have to deal with a big guy who wants to dong you because he won't do as he's told."
A stock market millionaire in the '80s, Glasheen was living the high life in Sydney as the chairman of a Sydney-based company that specialised in gold mining in Papua New Guinea.
At this stage he was worth a cool US$28.4 million, which he invested in luxury real estate along Sydney Harbour. But after the "Black Tuesday" crash (known to the rest of the world as the Black Monday crash) on October 19, 1987, the Dow Jones dropped a record 508 points, and subsequently, Glasheen's stock began to rapidly drop too.
"I got whacked, I wasn't aware it was going to happen. I should have sold the whole lot [of stocks]."
Glasheen lost $7.25 million that day alone, and the next few years would see his life spiral into bankruptcy and a broken family that couldn't be pieced back together; he divorced his wife in 1991.
By 1993, after the banks had moved in, Glasheen heard of a lease available on an undeveloped 64-acre island within a national park in Cape York, on Australia's remote peninsula: Restoration Island. The area has been described as the largest unspoilt wilderness in Northern Australia and one of the last remaining wilderness areas on Earth.
Feeling deserted on the mainland and looking for an excuse to leave, Glasheen walked away from his life and became Australia's real life Robinson Crusoe four years later, in 1997.
It was the perfect escape; except for the annual grocery shop to Cairns, Glasheen spends most of his time on the island, where he has lived in a renovated WWII outpost.
Despite his plans to build a health retreat on the island, he describes his home as a "bush camp" with a "five-star environment" and "half-star accommodation".
"There's not many people you can communicate with in this area, there's nothing to talk about," he said.
"That's really hard, probably the hardest thing."
But despite his seemingly remote situation, he has internet access, a mobile phone - and even plays the stock market.
"I'm trying to use my brains again," Glasheen explains.
"I'm trying to work miracles. So far, so good, I'm doing OK, nothing dramatic, but I think there are going to be terrific opportunities in the next couple of years."
He wishes he was smart enough to have picked up on the Bitcoin trend, ("I hesitated a couple years ago") but he has made some financial gains, thanks to a savvy conservative stock broker mate in Sydney who has "never had a wrong call yet".
He reads a lot, and has an opinion on everything from North Korea to Donald Trump.
"Someone has to do something, it can't keep going on the way it is," he says of the situation with North Korea.
"Something will go awfully wrong and most people just don't want to know about it.
"The rocket will reach this part of the world, they're already talking about Darwin because the Yanks are putting more people there.
"This isn't games, this is serious stuff."
In fact he bet on both Brexit and President Trump because you "get terrific odds if you do it a long time out".
"You take the odds when it seems ridiculous," he advises.
"I wouldn't call myself a Donald Trump fan but I think deep down he's trying to clean the swamp up. He's trying to, but whether he gets away with it or not, I don't know.
"If he can sort that bloke out in North Korea, he will be the God.
"I worry about it. I read about this stuff, what happens when a nuclear thing shoots off? You think, 'f*cking hell, this is more than just games. It's real'."
Yet ironically, it's money Glasheen says is "part of the illness in our society, there's no doubt about that".
Despite the doom and gloom he says he misses the small enjoyments of life. Live theatre, he says, "is a thing to treasure".
For Glasheen, this island existence is the perfect paradise. He says Australians are famously "mean", but wouldn't want to live any where else in the world. He has no motive to move back to the mainland, and plans to take his last breath here. He doesn't see the point of living "outside" of the island.
"I've been offered places elsewhere in other countries. I love Australia, it's a great country, it's just got a lot of stupid people, that's the problem.
"We don't appreciate how good the place is, it is one of the greatest places on earth, I don't know a better place and I've travelled a fair bit."
- news.com.au
