Dream Big, Win Big, and How Not to Lose Big

by Amy Sterling Casil

Financial Frequency. myCash

October 9, 2019 .3 min read

My great-aunt used to say she would win the lottery every day, although she was afraid that if she got a big windfall, "relatives" would appear out of nowhere and she would lose all the money if she ever won.

Sometimes it seems like every lottery winner ends up spending their winnings within a short time. It's untrue. There are some amazing lottery winners. Their successes can inspire you. You may never win the lottery but you can learn from these lucky and smart winners to plan for your own financial windfalls.

In 2012, 81-year-old Newport, Rhode Island resident Louise White was eating rainbow sherbet when she bought her $210 million lottery ticket. After consulting with legal and financial professionals, she started the Rainbow Sherbert Trust to offer her privacy and protect her winnings.

After Cynthia P. Stafford's brother was killed by a drunk driver, she took on the challenge of raising her brother's five children as a single mom. In 2007, Cynthia was working at a computer firm and living in a 1,100 square foot house with her brother's children. 

Cynthia credited the law of attraction for her $112 million lottery win. She slept with a note reading "$112 million" under her pillow and after three years won the Powerball jackpot she visualized. She met her family's financial needs and started her dream career as a film producer. 

Cynthia told Marie Claire that "You have to prepare yourself for wealth. You have to prepare for what is going to occur—at least as much as you can."

Cynthia was successful in preserving her winnings for nearly a decade. But in 2016, she filed for bankruptcy. Cynthia's film company had business setbacks, and some of her investments performed poorly. She told Piers Morgan "people have stolen from me." 

So what should you do if you win the lottery? Most financial planners say you should consult with an attorney and a financial planner before you cash in the ticket. Not only will you need to decide between a lump sum or an annuity, you'll want to preserve your privacy. 

Before you do anything with the money, give yourself some breathing room and time to think. This is solid advice for lottery winnings and other financial windfalls like an inheritance or a legal judgment.

Brad Duke, who won a $220 million Powerball prize in 2005 is often called the most level-headed Lottery winner. Duke continued to work as director at Gold's Gym for about three years after he won the lottery. He paid off his student loan and mortgage, traveled to Tahiti with 17 of his friends (the trip cost $63,000) and made a yearly gift to his family members of $12,000. 

Brad then set up a family foundation trust, invested $35 million in real estate, oil, and gas, and placed $45 million in low-risk, conservative investments including bonds.

He set a goal of becoming a billionaire using his lottery winnings. As of 2018, he reported he'd made about $100 million toward his goal. His primary advice today? "Take a breath and start thinking about who's going to help you to do the right thing."

Like Cynthia Stafford, Brad Duke thought about what he would do with a lot of money ahead of time. Both winners "visualized" not just their winnings but what they would plan to do afterward. One key difference? Brad continued to pursue his passion of cycling but didn't spend most of his winnings on it. Cynthia had always wanted to be in the film industry, but it's a notoriously tough business and her film company wasn't successful. 

Both of the winners helped their families and enjoyed good times with their friends, but moderately. A trip to Tahiti is a big splurge but moderate compared to Brad's overall net worth. Although Cynthia filed for bankruptcy, she kept the pool house she bought for her family in 2007. Located in Los Angeles' Pacific Palisades, Cynthia still has an asset in one of the country's wealthiest neighborhoods.

in this issue

  • safeguard your identity
  • date safe
  • cover your assets
  • protect yourself
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