More than 15 years ago, I got referred to a teacher and her husband who had just won the lottery. I’m not talking about a couple hundred bucks from a scratch-off ticket—they won the whole thing. The prize, before taxes, was probably around $50 million.
They asked me to come up to their house, and of course, I was happy to make the trip. When I got there, the wife greeted me warmly–gracious, welcoming, everything you’d hope for. She invited me inside, and there was her husband… sitting in a Stratolounger, facing the wall, back to me.
He didn’t want to be recognized. Not by the public or anyone. He was serious about privacy. So I’m introduced, and the wife is trying to be polite and get him to turn around and speak with me face-to-face unsuccessfully.
So there I was, doing one of the most awkward meetings of my career, talking to the back of a lounge chair. We never made eye contact. Never shook hands. The rapport, as you can imagine, wasn’t quite there. Needless to say, we didn’t end up working together.
Fast forward a few years, and I later learned they went through all the money. Boats, cars, second, third, and even fourth homes. The kind of spending spree that bites large chunks out of a seemingly inexhaustible estate. Plus, this was in New Jersey, where taxes can hit you pretty hard, pretty fast. The money and the marriage didn’t last. The wife even went back to teaching in the same school district as one of my clients—because she had to, not because she wanted to. She needed to support herself again and work long enough to earn her pension.
Looking back, I’m actually grateful I wasn’t hired. Sometimes things work out in unexpected ways.
Sudden Wealth Isn’t the Finish Line
Most of us won’t win the lottery, but sudden wealth still happens more often than people think. It might come from an inheritance, the sale of a business, a big bonus or stock grant, a legal settlement, or even viral success.
When it does, it often arrives without a plan.
That’s when things go sideways. People often overestimate how far their money will go, underestimate the impact of taxes, and let lifestyle inflation creep in quickly. The excitement is real, but so is the risk.
At Van Leeuwen & Company, we work with many first-generation wealth builders, and here’s what we help them do:
- Pause first. There’s rarely a need to make big decisions quickly.
- Build a team. Include the tax, legal, and financial professionals.
- Clarify goals. Money should support your life, not the other way around.
- Create guardrails. These are to protect against emotional decisions.
- Educate the family. No one wants their legacies to become burdens.
If you or someone you care about is facing a sudden financial windfall, help them slow down, get clarity, and plan with intention. Sudden wealth doesn’t have to be a cautionary tale. With the right guidance, it can be the start of something great.
Just maybe skip the recliner meetings.
Securities and advisory services offered through LPL Financial, a registered investment advisor, Member FINRA/SIPC.
Content in this material is for general information only and not intended to provide specific advice or recommendations for any individual