Lessons on Managing Life-Changing Money from Lotto Winners and Successful Retirees

In 1988, William Post won $16.2 million in the Pennsylvania lottery. A year later, he was $1 million in debt. First, he splurged: houses, cars, a plane. Then a former girlfriend sued him for a third of his winnings. His brother was arrested and convicted for hiring a hitman to kill Post and his then-wife in hopes that he'd inherit a share. And after sinking money into a failing family business, Post spent time in jail for firing a gun over the head of a bill collector. In the end, Post said he was happier living quietly on $450 a month and food stamps than he was when he was rich. Post's story is an extreme example of the bad decisions and bad luck that leave so many lotto winners wishing they'd never won at all. But while you're more likely to be struck by lightning than hit the winning numbers, an inheritance, a promotion, a legal settlement, selling a business, and reaching retirement can all create significant windfall scenarios as well. On today's show, we offer some tips on how to manage life-changing money, including tax planning, dealing with friends and family, and the kind of team that can help you protect your assets.

You can listen to Lessons on Managing Life-Changing Money from Lotto Winners and Successful Retirees online on Radio and Podcast. Open the player on this page to stream the available audio.

Lessons on Managing Life-Changing Money from Lotto Winners and Successful Retirees is an episode from Keen on Retirement by Bill Keen.

This episode is 35:05 long.

This episode was published on Oct 8, 2025.

Yes. Use the heart button on the episode page to add it to your favorite episodes list.

Yes. This page shows related episodes from Keen on Retirement when more episodes are available from the podcast feed.