On this episode of Simply Money presented by Allworth Financial, Bob and Brian reveal why your retirement plan may no longer match your reality—especially after three strong years in the market and inflation sticking around 3%. Then, the millionaire’s income problem: building wealth was the easy part—how you draw it down could make or break your retirement. The guys dig into Roth ladders, tax-smart income planning, and whether muni bonds or dividend portfolios really make sense at your tax bracket. Also tonight: Why your Social Security claiming strategy isn’t “set it and forget it,” how illiquid real estate could wreck your retirement flexibility, and the honest conversation every couple needs to have: “What happens if I die first?” Plus, practical tips on modernizing inherited investments, stress-testing DIY portfolios, and whether retiring overseas is really the dream—or a future headache.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian kick off the new year with the January Financial Stress Test: can your plan weather the unpredictability of 2026? With midterm elections looming, potential interest rate reversals, and market volatility ahead, they explore how to bulletproof your investments with strategies like bond duration diversification, buffered ETFs, and Monte Carlo simulations. Plus, they dive into the realities of long-term care insurance and what most investors miss. They also tackle your listener questions on Roth conversions, RMD strategies, and the best way to unwind concentrated stock positions. Finally, a lighthearted but eye-opening look at how eating out could silently devour your retirement nest egg.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian reveal why January is the most strategic money month of the year. From harvesting capital gains and revisiting direct indexing strategies to maximizing donor-advised funds and managing idle cash, they break down the smartest financial moves you can make right now. Plus, they discuss why a bigger tax refund isn't necessarily a good thing, how poor timing can erode your investment returns, and how to prepare emotionally and financially for long-term care decisions. Later, they answer listener questions about tax alpha, inherited IRAs, and consolidating retirement accounts.

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On this episode of Simply Money presented by Allworth Financial, Bob, Brian, and Allworth Chief Investment Officer Andy Stout dig into what the economy and the markets might hold in 2026. Plus, Bob and Brian dive into the cognitive and health risks of retiring too early, the financial tune-ups every empty nester should consider, and why having five advisors isn’t a financial strategy—it’s a coordination problem. Real-life stories, real retirement challenges, and advice that high-net-worth families won’t want to miss.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian reveal the four hidden forces that influence every major financial decision — even for the most seasoned, high-net-worth investors. Whether it's fear, guilt, social pressure, or family history, these emotional undercurrents can derail smart planning. Hear real-life stories, and learn how to spot and navigate the subconscious drivers behind your financial choices. Plus, what to do when a dinner table conversation exposes a blind spot in your plan, how to protect your wealth through a divorce, and the most common mistakes multi-millionaires are still making.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian challenge the traditional notion of retirement. Is it really about never working again? Or is the real dream having the freedom to work on your terms? They dig into why more high-net-worth families are choosing “financial flexibility” over full retirement, how to plan for that transition, and the hidden tax advantages that can make it work. Plus, the emotional—and often overlooked—decision to downsize your home, why clinging to old investments could hurt your future, and how a “retirement time machine” approach can help you make smarter money moves today.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian explore a simple phrase that could mean the difference between financial freedom and struggle: “the sooner the better.” They unpack new data around Gen X’s looming retirement crisis and what it means to be the first generation largely retiring without pensions. Then, they dive into a compelling new study showing how saving—not spending—could be the true key to financial happiness. Plus, career expert Julie Bauke joins to dissect “the executive dilemma”—when a promotion might not actually be the best next move. Finally, Bob and Brian answer real listener questions on managing capital gains, tapping into dividends, and planning for long-term care.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian take a deep dive into what really happened in 2025 — and why the investing fundamentals they shared all year long held up once again. From President Trump’s return and a new wave of tariffs, to a Federal Reserve caught between inflation and politics, to a stock market rally that rewarded patient investors — they told you what to expect, and they were right. Hear what mattered most, what moved the markets, and what lessons investors should take into 2026. Plus, the rise of real financial resolutions, how to measure if your money actually did its job this year, and your smart money questions answered.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down one of the biggest misconceptions in investing: risk. What most people think is risk—market ups and downs—is actually just volatility. The real risk? Overspending your retirement, missing out on growth, or playing it too safe. Bob and Brian walk through the critical differences, offer real-life examples with hard math, and explain how a misread on risk can jeopardize your long-term wealth. Plus, they share insights on stock market bubbles, lessons from the Vanderbilt family's fall from fortune, and whether Roth conversions make sense when you don’t need the money yet.

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