In the late 1990s, Chris Sacca used his student loan to start a company within the lawsuit industry - not to pay tuition. But he realized the idea was bad, he didn't have the skills needed, and he didn't have any investors. So before he ran out of money, he began day-trading stocks with the remaining money. This was during the buildup of the tech bubble so he made a huge profit from the trading. When the bubble exploded, his wealth decreased from 12 million to -2.8 million. His surroundings had convinced him that he was a stock market genius - so he thought he knew something. When the stock market crashed, he thought he was just unlucky. He was now 25 years old, no network, and had to find a way to make 2.8 million.
They've made a movie too.
Flooz was meant to be online currency that would serve as
an alternative to credit cards. It boggles the mind why
anyone would rather use an "online currency" than an actual
credit card, but that didn't stop Flooz from raising a
staggering $35 million from investors and signing up retail
giants such as Tower Records, Barnes & Noble, and
Restoration Hardware.
Masayoshi Son, of Softbank, hit a peak of $76 or so billion. Eventually dwindling down to $1.1 billion, a 'loss' of about $75 billion. Don't feel too bad for him though, perhaps fittingly given the discussion of a bubble again, he's back up to $16 billion in net worth and ascending (75% gain in wealth this past year).
Yasumitsu Shigeta was worth $42 billion at the peak of the bubble. Numerically he basically lost it all; what he had left was a rounding error. He was the founder of telecom company Hikari Tsushin. In 1999, he was Japan's youngest billionaire at 34. He's now back to being a billionaire again, 14 years later.
http://www.forbes.com/sites/forbesasia/2013/04/03/fifteen-ye...
http://www.modernluxury.com/san-francisco/story/workspace-ar...