How an Australian Millionaire Ended up Alone and Shirtless on a Tropical Island

In the 1980s David Glasheen was the chairman of a Sydney-based resource syndicate specializing in Papua New Guinean gold mining. He was also active in the stock market, amassing a fortune that peaked at around US $28.4 million, which he sank into luxury harbor-view real estate. That’s when the market sank him.

On October 19, 1987, the Dow Jones dropped a record 508 points, costing Glasheen about $7.25 million. This was the Black Monday crash (known as the Black Tuesday crash in Australia due to the time difference) that killed the 80s boom in a single day. But for Glasheen, the effects dragged on. “The next few years were really bloody hard,” he recalls. “My wife lost a lot of money, and she blamed me for most of it. Basically the family fell apart in 1991.” Glasheen ended up in court, lost, and then the banks moved in. By 1993 most of his money was gone, and he was looking for an escape.

Later that year, he met a woman from Zimbabwe who was recently divorced. They were at a similar place emotionally, he said, so when their friend mentioned an available lease at Restoration Island, an undeveloped 64-acre pristine island off the top of Australia’s east coast, they jumped at the opportunity and set up there in a little beachside shack. The plan, eventually, was to build a 60-room luxury resort.

“The idea didn’t last long,” Glasheen said. “She couldn’t handle it. It was all too tough for her.” After the woman left, he grew a beard and stopped wearing shirts. Soon after, he got bogged down in a war with the local Aborigines, who refused to let him build the resort. That’s when his shack became permanent. One by one, Glasheen’s dreams broke down into a kind of shipwrecked bankruptcy, which is how he still lives today: a tropical castaway, but one who still loves playing the market.

“The stock market is terrific,” says Glasheen, now 69 years old. “It’s the quickest, easiest way to make a dollar. It’s better than a job. You can earn 50 times the amount, in a tenth of the time.” Surprisingly, he doesn’t blame the market for his current situation. He was too rash, he says, allowing himself to get too deep. “I wasn’t smart enough to see it coming. I knew it was getting toppy, and I should have sold. But I didn’t, so I went down with the ship.”

For Glasheen, life on the island hasn’t been completely unpleasant. Over the last two decades he’s renovated a World War II outpost into a livable home, complete with solar power and internet. It’s an hour’s boat ride to the mainland for groceries, a trip he makes just a few times a year—he grows his own vegetables and catches fresh crabs and fish. He’s hosted numerous visitors, including Russell Crowe, who once moored his yacht and stayed for dinner.

Perhaps the only thing missing is a partner to share it with. Glasheen has posted ads on internet dating sites, looking for a girlfriend. “Nothing ever came of it really,” he laughs. “I had an Italian girl here for a short term. But she talked about an open relationship, and I didn’t know what that was. I thought it meant we didn’t have secrets.”

Glasheen says the best part of becoming a hermit has been the peace. “Restoration Island is a good name,” he said. “It’s restored me personally, in every which way.” Despite this, Glasheen still plays the market and praises uranium as a savvy investment. In this way, he’s not a hermit in the mold of Christopher McCandless, whose story became Into the Wild. Glasheen is more like a yuppie refugee than a naturalist. It’s clear he arrived at the island for a lack of options rather than for some grand ideology. Speaking with him, his head is still very much geared toward the investment world. When I ask for some investment advice, he’s more than forthcoming.

“Follow the [horse] jockeys,” he says. “If you know the managers and their track records, follow those people. If they’re consistently successful, you’ll make money. It’s all about errors. If you can stop your errors, and let the good ones run, you’ll make money. And start small. I’m a great believer in the pyramids, the bridge builders. They’ve all got one thing in common—they started from small beginnings. They’ve all made mistakes, and you’ve got to make mistakes too. You’ve got to lose it, but then you can make money.”

Or you could end up shirtless on a tropical island eating crabs all day long, which isn’t so bad either.