He searched for oil in the badlands of Somalia and fueled a stock market boom in Mongolia. He sued the world's smallest republic, far out in the Pacific, for a chunk of what it is worth.
Now, he is betting on North Korea.
James Passin, a hedge fund manager at Firebird Management, believes the nuclear-armed country sits on as much as a billion barrels of crude — enough to make it as big a producer as Oklahoma.
If the oil exists, he wants to help unlock it.
"You have a country with 25 million people — young, highly disciplined, literate — and a strong military-industrial complex," he said in an interview.
"It's possible that the early investors will be rewarded with potential for massive appreciation."
The risks of sinking cash — even just $7 million or so of Firebird's $700 million in assets — into a neo-Stalinist state with labor camps and virtually no private property are obvious.
The geopolitical volatility was on full display last week, as North Korea claimed that it had tested a hydrogen bomb.
And Mr. Passin is treading on murky investment territory, given the American sanctions against the country.
His investors have experienced the wild rides that come with such frontier markets.
Two of his funds are being liquidated after deep losses, including on banking in Iraq, gold in Armenia and oil and gas in Kenya.