Hugh O'Regan was never a real businessman in the ruthless profit-making at any cost mould. He was a visionary who could think no other way than outside the box.
He failed to foresee, however, the credit crunch and became one of the first to fall as the recession bit deeper.
Up until then, O'Regan's track record in business had been superb and marked by an uncanny ability to predict the next big thing.
O'Regan timed to perfection the sale of his Thomas Read chain of pubs for €30m. It was 2005, two years before the property bubble peaked and at a time when consumers were still flush with money.
The Dubliner had considerable cash and he was courted by Michael Fingleton's Irish Nationwide as well as Anglo Irish Bank who were anxious to lend him more money based on his visionary track record.
O'Regan was never interested in money in the conventional way when he had plenty of it in his bank account. Quietly, he gave millions away during the lull before Ireland's economy tanked.
For example, he refurbished a beautiful building on St Stephen's Green and encouraged emerging charities such as youth volunteering organisation Suas Educational Development and GESCI, a UN-backed non-governmental organisation, to bring computers to Africa; and others by offering them low rents at a time when they were sky-high in Dublin city centre.
He was also an early mentor to Paddy Cosgrave, the founder of the Dublin Web Summit, which has helped bring international names such as Twitter to Dublin.
Having transformed the Dublin pub business he then felt free to pursue his great dream. It would also, sadly, prove to be his biggest financial loadstone.
Along the Dublin-Enniskerry road lay the Kilternan hotel where Muhammad Ali had trained prior to his only Dublin fight in 1972 against Al 'Blue' Lewis. The hotel had fallen out of favour in the decades afterwards, but O'Regan saw potential there, so he bought it for €12.7m from philanthropist Chuck Feeney.
The hotel had earned him a small income from its artificial ski slope as O'Regan painstakingly guided it through the planning process.
He was determined to build a massive high-end hotel, leisure and conference centre resort there and he turned to Michael Fingleton's Irish Nationwide for the money.
In the space of just three years his borrowings from the society grew from €33m to more than €180m.
About €150m of this went into Kilternan to which he had now added plans for a theatre and innovation campus. His plan was bold and like nothing the country had seen before.
He also took on another €30m to buy a site in Cobh, Co Cork. O'Regan loved the picturesque small town, where the Titanic had stopped off on its tragic voyage, and he began to work on plans to build 1,200 homes there.
At the same time, O'Regan built up his borrowings from Anglo Irish Bank. In total, he borrowed €80m from it, some of which he used to buy the former Hibernian United Services Club building at 8 St Stephen's Green, and which he planned to turn into a new social club.
He was badly exposed in his project's development cycle when the music stopped in 2008 and the credit crunch really hit home.
His banks, however, refused to play ball and instead began to appoint receivers to his companies, wrenching his assets from him.
Yet, what he achieved in helping create Dublin's pub scene, building and refurbishing some of its better buildings, and inspiring people to test their own limits, will last for many years to come.