On this episode of Simply Money presented by Allworth Financial, Bob and Brian pull up a booth at your favorite Saturday morning diner—where three strangers each worth around $3 million reveal just how wildly different financial lives can look. Meet Jim, a newly retired corporate lifer trying to make his nest egg last; Maria, a successful business owner staring down a big liquidity event; and Chris, a laid-back heir with a taste for risky bets. Despite similar net worths, their challenges—and mindsets—couldn't be more different.

The guys break down three key financial stressors: market headlines, long-term care fears, and major downturns—and how each person reacts. From Roth conversions and tax planning to installment sales and speculative investing, this episode is packed with real-world examples of why your wealth story needs its own unique plan.