Money management is key, people! You can have the fattest wallet in the world, but things can disappear pretty quickly if you’re not on top of your finances.

The Daily Beast has highlighted a number of big money-makers who managed to lose it all.

Paulo Mendonça

Less than three years ago, the chief executive of OGX Petróleo, known as “Dr Oil,” was on his way to becoming one of the world’s richest men. But when OGX, of which he was both CEO and a major investor, was only able to deliver 15,000 barrels of oil a day rather than the 750,000 he had claimed, its share price plunged 90 percent. Mendonça’s own fortune declined commensurately; according to Forbes, he lost more than $25 billion in the course of a few months.

Kim Dotcom

The founder of Megauzpload, an online file sharing service, was, briefly, worth many millions, but, having moved to New Zealand in 2010, he is now facing extradition to the US over alleged copyright infringement. He shelled out around $400,000 to sponsor fireworks welcoming in 2011 in New Zealand’s biggest city, Auckland, and set up a political party, the Internet Mana alliance, spending over $3 million in a failed attempt to win a seat in New Zealand’s 120-seat parliament. Kim is not thought to be broke just yet, but he will be soon, as movie studios seek to recoup $100m in copyright fees.

Nelson Bunker Hunt

Nelson Bunker Hunt, the Texan oilman who ruthlessly attempted to “corner” the silver market and was once worth up to $16 billion, but ended his days (he died last week at the age of 88) in mightily reduced circumstances, living in a modest suburban house on the outskirts of Dallas.

Bunker started buying silver in 1970, when it was $1.94 an ounce. By January 1980, along with 1,000 racehorses and they had the rights via options to 200 million ounces, and it was worth $50 an ounce (let us do the math for you—they controlled $10bn of the stuff). Only one problem—their holding was so vast that they could not sell off any meaningful percentage of their horde without driving down the price. This they found out over the following months.

Check out the full list on the Daily Beast.

While the above businessmen were able to somehow lose all their riches, winning some money is definitely easier than losing it these days. The Megamillions lottery has rolled over to $252 Million (R2.8 Billion). You can get tickets for tomorrow’s draw here.