But Gianluca Vacchi, 50, had his yacht and several properties seized by creditors - much to the amusement of the Internet.
The tattooed, body-building heir to an industrial empire fills his social media with a cash-rich, work-free existence dedicated to the pursuit of pleasure.
But now his lavish lifestyle is being remorselessly parodied on the internet. Twitter users have posted pictures of themselves posing, Vacchi-style in front of plastic paddling pools and pedalos, while a Facebook page entitled 'Find Gianluca Vacchi a job' has attracted a huge following.
With his penchants for classic cars and private jet, he made '#Enjoy' his online catchphrase and the title of a self-congratulatory book he published last year.
He recounts after 20 years of hard work in the family business, he had had an epiphany and decided to give it up.
Instead, he choose to cavort pool-side with the likes of his current paramour, Ariadna Gutierrez, a former Miss Colombia.
So inevitably social media users were amused that Vacchi has had a yacht and several villas seized by banks demanding repayment of debts of 10.5 million euros.
His stake in a golf course near Bologna has also been confiscated pending an arrangement with creditors who fear other debts may have been hidden, the Quotidiano Nazionale reported.
Vacchi claimed, 'It is just a little debt,' when set against the value of the family business, IMA, a conglomerate with interests in packaging and pharmaceuticals.
The playboy's stake reportedly generates dividends of five million euros a year.
However, it seems that may not have been enough to sustain a lifestyle now being mercilessly parodied on the web.
An appeal for funds to pay off Vacchi's has not done so well: by Friday it had only attracted pledges of five euros.
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