On this episode of Simply Money presented by Allworth Financial, Bob and Brian reveal what wealthy families are doing in December that most people completely overlook. While many go into coast mode during the holidays, high-net-worth individuals are making smart year-end moves—rebalancing their portfolios, harvesting tax losses (and gains), and donating appreciated assets through donor-advised funds.

They’ll also explain why December is the perfect time to talk to your kids about your estate plan, how to take advantage of qualified charitable distributions from your IRA if you're over age 70½, and how to gift money to your family now—completely tax-free. Plus, they tie it all together with a powerful message about using the holidays to pass on your values, not just your wealth.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian introduce the “financial freedom test drive”—a bold way to rehearse retirement before you take the plunge. Learn why trying out your withdrawal strategy and lifestyle early could save you from major surprises later. Then, they tackle the “millionaire’s income problem,” where pulling money out of your portfolio the wrong way can cost you in taxes, Medicare premiums, and peace of mind.

They’ll cover Roth conversion ladders, municipal bonds, rental income strategies, and real-world withdrawal tactics for people with significant assets. Plus, the guys share the uncomfortable but crucial conversation every couple should have: “What happens if I die first?” And finally, they break down the dream—and reality—of retiring overseas. From taxes to healthcare to missing Elder football games, this episode is packed with practical insight for high-net-worth families preparing for the next chapter.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian ask a powerful question: Are you just building wealth, or are you building a life? They explore the concept of "Return on Life" — and how many successful, high-net-worth families struggle to shift from accumulation to enjoyment. Through real stories and actionable advice, they help you confront financial fear, lifestyle paralysis, and the emotional habits that could be holding you back from a meaningful retirement. Plus, the surprising move from Vanguard that could bring crypto into the mainstream, a snapshot of the Cincinnati housing market, and how to plan around Medicare’s IRMAA surcharges.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian reveal a stunning stat: just two companies—Alphabet and Nvidia—are responsible for a third of the S&P 500’s returns this year. If you think you’re diversified just because you own an index fund, think again. They dive into the historical precedent for today’s market concentration, the real risks of overexposure to big tech, and what smart investors should consider instead—including equal-weight ETFs, buffered products, and direct indexing.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian dive into the latest economic data with Allworth’s Chief Investment Officer Andy Stout — who explains why the Fed might be flying blind without key data and what that means for interest rates, inflation, and your investments. Plus, find out why a growing number of AI tools are managing portfolios — and whether that's a smart move or a costly mistake, especially for high-net-worth investors. The guys also explore how Baby Boomers amassed $85 trillion in wealth and the critical financial lessons younger generations need to hear. And, what do you do when your spouse wants to gamble on individual stocks — and you don’t? They’ll tackle portfolio complexity, tax inefficiency, and the rising trend of adult kids moving back in with Mom and Dad.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down what most investors misunderstand about “risk” — and how that confusion could cost you more than any market drop ever will. They explore the real definition of risk, why sitting in cash might be riskier than you think, and how to create a retirement plan that accounts for volatility without derailing your future. Plus, hear why stock market bubbles might not be all bad (if you’re prepared), and what the Vanderbilt family can teach you about preserving wealth for generations. Later, in Ask the Advisor, they answer your questions about Roth conversions, gifting to children, charitable giving, and what to do with a large cash windfall. And in Brian’s Bottom Line, the essential estate planning move everyone should double-check today.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian challenge the traditional idea of retirement by asking: what if financial freedom isn’t about quitting work forever, but having the power to choose how you work, when, and with whom? They dive into the growing trend of financial flexibility and how high-net-worth individuals are redefining their retirement goals. From part-time consulting at GE to opening woodshops or working at Costco for healthcare, the conversation covers how purpose, planning, and portfolio management play a role in these transitions. Plus, they explain how to fund this lifestyle shift with smarter income strategies, tax diversification, and tools like the Rule of 55. Later in the show, they explore why clinging to outdated investments might be holding your financial plan back, how to think differently about downsizing your home, and why your future success often comes down to basic math.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian dive into the four hidden forces that subtly guide every high-stakes financial decision—especially for those with significant wealth. From emotional hang-ups and generational money mindsets to the quiet pressures of social comparison and analysis paralysis, the guys break down how even the most financially savvy families can be influenced in ways that spreadsheets can’t predict. Plus, they tackle the biggest financial mistakes successful investors admit to behind closed doors, reveal how divorce can wreck your retirement plan if you're not careful, and answer listener questions on annuities, private credit, and more.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian put on their “tough teacher hats” to deliver some advice you may not want to hear, but absolutely need to hear. Just because you’ve saved $2 million, $3 million, or even $5 million doesn’t mean you’re automatically set for life. Their lessons cover why retirement isn’t a vacation but a paycheck replacement plan, why your kids don’t need another check but a financial strategy, how treating your portfolio like a casino can wreck decades of hard work, and why taxes could cost you more than your house. Plus, they dive into the real spending patterns of retirees, scams targeting families, and listener questions on concentrated tech stock, charitable remainder trusts, and how to plan for estate taxes on illiquid assets like real estate.

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