On this episode of Simply Money presented by Allworth Financial, Bob and Brian expose the hidden financial risks that even financially comfortable families often overlook — like gaps in liability protection, cyber threats, and uncoordinated estate plans. They unpack why an umbrella insurance policy is a must-have, especially if your net worth has made you a target. Then, are your investments really diversified — or just duplicated? They dig into how overlapping holdings in your accounts could leave you vulnerable in a downturn, and what true diversification actually looks like.

Plus, they tackle the emotional side of money: how to fireproof your finances from family drama, whether it's sibling tensions over a family business or preparing for generational wealth transfer. And for anyone with too much company stock, they explore smart, tax-efficient ways to unwind concentrated positions and protect your portfolio from unnecessary risk.