10 Smartest Lottery Winners And How They Stayed Rich
We've all heard the horror stories. Huge lottery wins blown on cars, parties, and bad business ideas. But not everyone flames out. A handful of winners treated their jackpots like seed capital, built systems, and kept a low profile. Here are 10 of the smartest lottery winners and what they did differently.
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10) John & Lisa Robinson — Privacy Lessons From A Record Powerball
Win: Share of the historic $1.586B Powerball (about $528M each before split); took a $327.8M lump sum pre-tax.
Smart move: After going public on national TV (on an attorney's advice), they learned the hard way how valuable privacy is. They relocated, bought a secure property, and shifted to quiet real-estate investing rather than splashy purchases.
Takeaway: If your state allows any privacy structuring, use it. Limit publicity. Invest in assets you understand.
9) Lerynne West — Structure First, Generosity With Boundaries
Win: Powerball share for $343.9M (annuity) but chose lump sum around $140.6M after taxes.
Smart move: Hired a wealth manager, set specific amounts for family support, funded grandkids' college, donated $500K to the Travis Mills Foundation, and launched The Callum Foundation.
Takeaway: Put guardrails around giving, then automate the mission with a foundation.
8) Cynthia Stafford — Real Estate + Film Investments
Win: $112M (California).
Smart move: Shared some with family, then focused on real estate and built Queen Nefertari Productions LLC, backing multiple films while hosting a charity-focused show.
Takeaway: Invest in cash-flowing assets and a passion business with a plan.
7) Brad Duke — From Spin Class To A Scaled Portfolio
Win: Reported as a huge jackpot (took ~$74M after taxes via lump sum).
Smart move: Researched other winners, set a long-term growth target, paid off debt, funded family, then assembled a team to invest across energy, real estate, and fitness, plus low-risk bonds and a family foundation.
Takeaway: Build an investment committee mindset. Pay yourself stability first, then scale.
6) Jason Fry — Buy Fun, Then Buy Cash Flow
Win: $14M (Florida), took $13.6M lump sum.
Smart move: After early splurges, he bought Batteries Plus franchise locations and a golf driving range generating steady revenue, then kept expanding.
Takeaway: A couple toys are fine. The engine is operating businesses.
5) Peter Lavery — Tripling Up Through Whiskey And Property
Win: £10.2M (UK National Lottery).
Smart move: Said no to most handout requests, then revived a local distillery, created the Danny Boy brand, and accumulated 30+ properties.
Takeaway: Be selective with requests. Reinvent local industries and compound with real estate.
4) Sue Herdman — The Unlikely Pig-Farm Mogul
Win: ~£1.2M (UK).
Smart move: Kept quiet for months, then sold her salon and invested with her partner in the family pig farm in North Yorkshire. Today it's a 7,000-pig operation with strong community impact.
Takeaway: Modest jackpot? Go where you have leverage and operational know-how.
3) Mark & Cheryl Brutenell — Lifestyle, Then A Lasting Business
Win: Share of £7.9M (Camelot), about £916,915.
Smart move: Enjoyed some years off, moved to a better home, then invested in a double-glazing company that's still profitable decades later.
Takeaway: You can enjoy the win and still build a durable income stream.
2) Yancy Hicks — From Crew Member To Owner
Win: $1M (2008).
Smart move: Stayed at McDonald's for four months while planning, bought a Subway franchise, and set up college savings for his daughter.
Takeaway: If you know an industry from the ground up, ownership can flip your financial life.
1) Richard Lustig — Turned Wins Into A Brand
Win: Seven smaller wins totaling around $1M.
Smart move: Monetized the media spotlight with a book and software, became a regular at lottery events, and built a business around his expertise.
Takeaway: When the spotlight finds you, package your story and sell the playbook.
Common Patterns Of "Smart" Lottery Winners
- Privacy and planning: Limit exposure. Photograph the ticket front/back. Store it safely at home. Consult an attorney before signing.
- Lump sum, then structure: Pay taxes once, build a diversified portfolio, and put written rules around gifts.
- Cash-flow assets: Franchises, real estate, operating businesses, and dividend stocks beat lifestyle inflation.
- Philanthropy with systems: Foundations and donor-advised funds channel generosity without chaos.
- Say "no" cleanly: Clear boundaries protect relationships and wealth.
Final Word
Winning the lottery is chance. Staying wealthy is choice. The winners above made moves any windfall recipient can copy: buy boring cash flow, keep a low profile, put rules around giving, and turn the spotlight into a platform.
Ready to Try Your Luck?
Learn from the smartest winners and use our honest lottery generators to pick your numbers.