Bets on debt-ravaged Greece or ailing phone maker BlackBerry would make many investors flee, but for Prem Watsa both are part of a “cautious” strategy he employs to manage Fairfax Financial’s $23.3 billion portfolio.

Indian-born Watsa, 63, often compared to U.S. investor Warren Buffet, another self-made man, prides himself on a strategy of investing in stocks and markets others avoid.

In 1990, he was on the right side of the Tokyo market crash, and seventeen years later, his bet against the U.S. housing market bubble left him with billions of dollars in profits while less prescient peers took a battering.

His 2011 investment in Bank of Ireland—the only domestic Irish bank not forced into state ownership after a financial crisis—has almost trebled in value to 845 million euros ($1.15 billion).

Investments in Greece and a $4.7 billion bid for BlackBerry, which has faded almost to irrelevance in a competitive smartphone market, fit the pattern of contrarian investments, but it’s too early to say if they will succeed.

“We’ve got lots of cash, we’ve got 30 percent cash,” Watsa told Reuters in a rare interview by telephone on Friday, referring to the portion of his fund that is invested in cash.

The high cash exposure comes despite record low interest rates as central banks on both sides of the Atlantic implement quantitative easing (QE) to pump economies with cheap money.

Reticent about what many investors have seen as the bet of the year in U.S. equities, where the broad S&P500 index of leading shares has gained more than 26 percent so far in 2013, Watsa said the market was overstretched.

“We’re quite concerned about the U.S. markets in terms of how high they have gone. It’s not often that we put our money at risk. We’re very cautious, broadly speaking, in the investment business,” he said.

“At least in the United States and Europe, inflation has yet to come up in any significant way … in both areas it’s close to 50 year lows in spite of all of the central bank action. We worry about those kinds of things.”

High Hopes For Ireland

Watsa spends considerably less time worrying about Ireland, where he said he had invested about 700 million dollars on property investments and his Bank of Ireland stake (at a cost of about 300 million euros, or $407.63 million).

The country was in the first year of its sovereign bailout when Watsa and Bill McMorrow, head of U.S.-headquartered real estate investor Kennedy Wilson, brought together five investors who pumped 1.1 billion euros into the bank’s 2011 bailout.

The yield on Ireland’s benchmark 10 year bond topped 13 percent and Bank of Ireland’s main rival AIB had to accept a bailout that left it 99.8 percent state-owned as the country plumbed the depths of its financial crisis.

Less than three years after, Ireland is within days of exiting its sovereign bailout, its 10-year bonds are commanding an interest rate of about 3.5 percent, unemployment is falling and property prices are starting to creep higher.

Watsa said he was not concerned about the country’s decision to go it alone and exit its bailout without a safety net – or precautionary credit line.

“The Irish have taken the tough medicine without any riots, without any noise, and have really done it very well,” he said.

“We continue to look at the possibilities. We met many business people in Ireland, we have huge admiration for the business community in Ireland.”

Watsa, who’s only experience in Ireland prior to the bank deal was serving as best man at a friend’s wedding in the five-star K Club golf resort an hour from Dublin, travelled to Dublin monthly for Bank of Ireland board meetings while a director.

He stepped down in July, passing the baton to a Fairfax colleague Bradley Martin, with fond memories.

“I rarely get on boards and I don’t stay on them for long – I have enough things to do in Fairfax,” he said, adding that he enjoyed the jokes. “The Irish people never lose a moment to have a good laugh. Even if it’s on their own account.”

Audacious Picks

Ireland may have the humor, but it is not the only crisis-hit eurozone economy that has taken Watsa’s fancy.

“We like Ireland and we also like Greece,” he said, adding that Prime Minister Antonis Samaras was doing a very good job.

Fairfax was linked with an investment in National Bank of Greece in March, when the bank said the Canadian investor had “expressed interest” in the recapitalization.

Fairfax did not ultimately participate, but in October Watsa’s company announced it would increase its stake in property company Eurobank Properties from 19 to 41 percent in a share issue expected to be carried out in April 2014.

Fairfax has been tipped as a possible investor in its parent company Eurobank, where the Greek authorities are trying to find anchor investors to take part in a 2 billion euros capital raise.

“We’ve made many investments in common stock in Greece, and Eurobank Properties … and of course we’ll look at other opportunities in Greece,” said Watsa, declining to comment on Eurobank specifically.

The bid for BlackBerry was by far his most audacious play of 2013. He failed to raise enough finance for the $4.7 billion bid to take the firm private, and instead led a consortium that funded a $1 billion loan to fund a turn-around.

Management has been overhauled including the Nov. 25 appointment of an interim chief executive John Chen who Watsa said would be there for the “long haul”.

“You never look back, you deal with the hand that you have, there’s no use looking at whether you can get four aces or a flush, you deal with the hand that you have,” he said.

“We think BlackBerry is an iconic company, an iconic brand, it’s known worldwide … it’s a company that deserves to exist and with John Chen it will.”

But he may have to persuade some of his Irish friends. Richie Boucher, chief executive of the Bank of Ireland, who Watsa effusively praises, for one is a devoted iPhone user. “I guess the Bank of Ireland are not perfect,” Watsa laughed.

(Reporting By Laura Noonan, additional reporting by Janet Guttsman in Tornoto, editing by Elizabeth Piper)