David Glasheen, 81, has been marooned, by his own choice, on a remote island in northern Australia for 27 years. Before he moved to this island, he was a successful entrepreneur worth nearly $30m on paper. He had two yachts, owned multiple waterfront properties, and lived what they call "the good life".
Today, he lives alone for long stretches at a time, rarely returning to the mainland. He sports a sea-swept white beard and forages for oysters barefoot and shirtless. His only permanent companions are two mannequins named Miranda and Phyllis. Miranda was sourced from a junkyard for $10 and named after a character in Shakespeare’s "The Tempest". They reside in his main residence, but the relationship is strictly platonic ("I do not have sexual relations with them", he clarified in the book "The Millionaire Castaway" which he co-wrote in 2019).
Forty years go, David Glasheen was at the peak of a successful career in business. He raised $2 million in capital to start a mining exploration firm that later went public on the Australian Securities Exchange. In the boom of the 1980s, the shares in his newly-formed company soared from 25 cents to $1.40. On paper, his net worth was in the tens of millions.
But the good times didn’t last. On Monday, October 19, 1987, Wall Street crashed, wiping out more than $500 billion in capital in 24 hours. The next day, the Australian market followed suit and David watched helplessly as his shares dropped from $.140 to $0.28, then to $0.02.
And things got worse. Glasheen had been borrowing heavily on his properties to purchase more stock. The banks came knocking. By 1991, he was evicted from his home, rendering him "homeless and penniless". His marriage broke up and he started drinking.
For several years, he slept on friends' couches. Eventually, he moved in with a beauty salon owner named Denika and tried to settle back into domestic life. Soon, he found himself yearning for some kind of escape.
Then an old-friend-turned-real-estate-agent told him about a remote island. The island in question, Restoration Island, was near the northern tip of Queensland, a good 2,000 miles from Sydney. It could only be accessed via several flights in twin-propeller planes, a 25-mile drive over bumpy dirt roads, and a 15-minute boat ride from the mainland.
Glasheen first visited “Resto” in 1993, and he was at once enchanted and distraught. It was like an island out of a cartoon of paradise: white sands, palm trees, turquoise waters. It was also in a state of disrepair, strewn with trash and crumbling structures.
A consortium of businessmen had purchased a 30-year lease on the island in 1979 for $156,000. In 1989, they’d negotiated an extension to 50 years, in exchange for giving back two-thirds of the island that was uninhabitable to the nearby native Kuuku Ya’u people. Now, these businessmen were looking to sell their stake for the sum of $1.2 million. Glasheen didn’t have the money but he was able to convince a few investor friends to put up enough to sublease the habitable third of Resto. Eventually, he secured one of eight shares in the island, under the agreement that he and his partners would develop the land.
in 1997, Glasheen packed a small suitcase with a few shirts, some board shorts, a torch, and toiletries, and decided to move there on his own.
He never truly came back. Listen to his story here.
