NEW YORK (CNN/Money) - Even before he turned in his lucky ticket, William Post had a hunch that winning the $16-million Pennsylvania Lottery jackpot was going to bring him a heap of trouble. He just didn't know how much.

"With my family, [I knew] they were going to do anything to get the money," said Post, 63, who won big back on Feb. 24, 1988.

As it turned out, anything included a younger brother who was arrested for hiring a hit man to kill Post. Other siblings, said Post, pestered him until he agreed to invest in various car and restaurant business deals. He says he never saw a dime of it back.

But that wasn't the end.

"I had more lawsuits than you could shake a stick at," said Post.

A former girlfriend sued Post for failing to share winnings. Meanwhile, courts held his money in escrow until Post's debts were settled. Eventually, he auctioned off his winning ticket to pay his bills. All in all, Post says he figures he received about $2 million, part of which he used to buy his three-bedroom Pennsylvania home.

It's about the only thing he has to show for the Lottery winnings. All the money is gone. Legal fees and taxes ate much of the money, says Post. But he's also admitted that he went on a spending spree, too.

Post now lives on $450 monthly Social Security payments and food stamps. He spends much of his day watching classic movies on television. But Post isn't complaining. Now that the money's gone, people leave him alone. His house is quiet.

He's content.

"I've got peace of mind and you never realize how valuable it is until you lose it," he says. "I'm a Roman Catholic so I know that rarely a rich man goes to heaven. The way I see it, I've got a good shot."

As it turns out, Post is in good company among lottery winners gone bust. One New Jersey woman even won two lotteries -- for a total of $5.4 million -- but blew threw it all on spending, gifts and gambling. Uncommon? Not really.

Two out of three lose or spend all their winnings within five years, said Stephen Goldbart, co-director of the Money, Meaning and Choices Institute in San Francisco.

Most lottery winners spend all their winnings because they don't make careful plans to save or invest it, he notes.

"The average American lives paycheck to paycheck," he adds. "So when they come into sudden wealth, they have to learn the financial ropes" of planning.

But lottery winners aren't the only ones who botch sudden wealth. Lately, Goldbart and his colleague, Joan Invursky DiFuria, have been counseling dot.com whiz kids who made millions -- then lost it all -- when the tech bubble burst. While many spent their newfound fortune on lavish parties, fancy cars, homes and other toys, most of their money was paper wealth invested in just one or a handful of dot.com stock.

"They didn't protect themselves against change and they didn't diversify," said DiFuria. "It was unexpected that they'd make so much so quickly, and it was unexpected that they'd lose so much so quickly."

For many, the sudden loss packed a bitter punch -- creating pressure to earn new fortunes. Others are stuck in the soul-searching phase, wondering where to now and how to apply their skills toward a meaningful line of work. Still, others adjusted surprisingly well, said DiFuria.

She remembers the day she met with one woman in her late 20's who had just learned that she owed more than $500,000 in taxes on stock options she exercised but never cashed in.

"She had a great attitude," DiFuria said. "She said, 'You know, the money never seemed real to me. I'm a little relieved. My friends won't be pointing at me anymore.' When she drove to work in her new car she felt great because everyone else had one. But when she returned to her middle-class neighborhood, she felt uncomfortable. She felt isolated."

Peter Grandich never felt isolated when he had millions. On the contrary, he loved what money could buy -- a spacious mansion in New Jersey, two race cars, five race horses and lots of time on the golf course.

"I was addicted to the game," said Grandich, a high school dropout who made his fortune on Wall Street. (His first break came when he was a warehouse manager and a security guard told him about a stock tip. Grandich used $7,000 of his family's wedding money and made $20,000).

Grandich eventually became a broker, but because he hated cold calling, he started a newsletter to keep himself busy at work. Again, luck was with Grandich when he moved clients out of the market before it collapsed in October 1987. His bearish call secured Grandich's reputation as the dropout/whiz kid who made good. Grandich was quoted in national papers and appeared on television -- living the good life. He calls it his "arrogant days."

"I was playing golf, making deals. I probably gave more money away in gifts and parties than I dreamed of making when I was a warehouse manager," he said.

Hubris finally got the better of him in 1997, when Grandich had his own firm and, among other things, was raising money for various mining companies. That was when the Bre-X gold mining scandal exploded. Bre-X, a small Canadian mining company, had wowed investors around the world when it claimed to have tapped the world's biggest gold mine deep in the Indonesian jungle, but the find turned out to be a massive hoax. The scandal put a chill on Grandich's business. But instead of calling it quits, he used his own money to prop up his failing deals.

"I lost 75 percent of what I had in less than a year," he recalls. "Some people get suckered by their own actions, their own greed -- that was me."

Grandich was so depressed he even considered suicide, but then worried he wouldn't be able to afford the care if he permanently injured himself. Filled with despair, he started looking for answers.

He drove to Barnes & Noble.

Grandich planned to buy a book on business strategies -- or mental health. But he ended up picking up a Bible. By his own estimates, 25 percent of the Bible's passages dealt with money.

It was a sign. And it led him to start Trinity Financial, Sports & Entertainment Co. -- a financial services business. Grandich's partner is Lee Rouson, the former New York Giants running back and a Christian leader with Sports World Ministries.

The duo now aim to help their clients -- who include players in the National Football League -- make informed, Christian-oriented financial decisions.

As it turns out, there are plenty of young football players who, like Grandich, have made then lost fortunes. In fact the NFL estimates that 78 players have been defrauded at least $42 million in the last three years. In response, the NFL Players Association this year launched a rigorous screening and certification program, with input from the Security and Exchange Commission, for financial advisers who want to register to work with the union's members, including players and coaches. (Note: anyone can call himself a financial planner, so whether you're a star athlete or a weekend warrior, choose your adviser carefully. For some guidance, see the Money lesson on hiring a financial planner.)

Meanwhile, Grandich sees a bright future for himself and his clients.

"I can manage their money but I won't throw up all sorts of big numbers," he says. "They won't have high reward, but they won't have high risk either. If they like the idea of turning $20,000 into $100,000 in five years, I'm not the right person."

Grandich pauses. "I had a tremendous home. I gave away $150,000 one year. I was like a kid in a candy store. But I don't think I had one-tenth the fun [that] I'm having today."