The holiday season may have most of us ready to slow down, but the stakes for Wednesday night’s Powerball are just heating up. The top prize for Wednesday night’s drawing is estimated to be $1.7 billion, making it the sixth-largest jackpot in Powerball history.
If there is a winner on Wednesday, it could feel like a Christmas miracle, but former Powerball winner, Timothy Shultz, said there’s also a slim chance of going broke within a few years, despite amassing that amount of wealth.
Schultz won $28 million in 1999 while working at a gas station and retired a multimillionaire by the age of 21. In an effort not to become one of the unfortunate winners who eventually lose it all, he put a specific plan in place.
Consulting wealth professionals is the first step Schultz took after winning the Powerball
“Suddenly, I’d gone from a gas station attendant to retired at 21,” Shultz told Business Insider in a 2024 interview. “I felt like I was holding a magic wand. Everything was possible, but I also wanted to be financially responsible.”
He said, “At 21, I had no idea what to do with that kind of money and was lucky I sought professional guidance. I didn’t want to become a statistic of lottery winners going broke within a few years.”
Before turning in the ticket, he said he consulted with wealth professionals to understand how much he could afford to spend and give to others. “I helped many people, but also wanted to live within my means.”
Investing the money helped him maintain his wealth
Before he received any of the money, he established a plan with advisors to invest it conservatively, ensuring the returns could last him a lifetime. “I mostly invested in stocks, bonds, and mutual funds,” he said.
Emily Irwin, a Wells Fargo advisor who guides lottery winners on how to spend their money, told Business Insider in a 2023 interview that this is exactly what winners should do.
She also advised assembling a team of financial planners as soon as possible and that, “You must carefully consider experts specializing in high-net-worth and ultra-high-net-worth tax planning.” Irwin also said winners should interview several candidates, as these advisors will most likely be in their lives for years.
Other ways the 1999 Powerball winner spent his money
The first thing Shultz purchased with the money was the latest video game system. A luxury, he said, he “couldn’t afford before winning.” The next thing he did was set up his investments.
After establishing his investments, Schultz said he helped his family, bought vehicles, and traveled. He even went back to college to study film and broadcast journalism, a dream come true for him
But after winning, and still being surrounded by other struggling college students, Shultz felt pressure to pay for friends’ vacations, meals, or anything they did together.
He said, “When you win the lottery, people don’t view the money as something you’ve earned. A family member explicitly told me I got something for nothing by winning the lottery and should keep giving them and others money.”
Despite his successful investments, he still has one regret
These days, Schultz said he spends most of his free time exercising and working on his podcast and YouTube channel, “Lottery, Dreams, and Fortune,” which highlights the story of other lottery winners. “YouTube brings in some money, but I can live off my investments,” he said.
Despite making great investment choices, Schultz still regrets overlooking one specific investment.”I wish I had invested in bitcoin a few years ago, but that’s my only regret about how I’ve spent the winnings,” he said.
Still, Shultz’s initial decision to seek professional financial help set him up for years of success.
Correction: December 23, 2025 —An earlier version of this story misstated the details of the next Powerball drawing. It is for $1.7 billion on Wednesday night.
