Simply Money

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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On this episode of Simply Money presented by Allworth Financial, Bob and Brian uncover the #1 mistake even successful savers and investors make: accumulating assets without a real strategy. They dig into what it means to truly have a plan — from organizing scattered accounts, to transitioning from mutual funds to tax-efficient ETFs, and dealing with concentrated stock positions using tools like direct indexing, exchange funds, and collars. Plus, they break down how buffered ETFs can provide downside protection when the market turns, how to avoid overspending in the first 10 years of retirement, and why automated investing might fail you after age 60. Finally, a five-minute task that could save you from financial fraud: how and why to freeze your credit today.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian take a deep dive into the surprising ways your brain might be sabotaging your financial future. From action bias and overconfidence to herd mentality and confirmation bias, they reveal how emotional traps become even more dangerous the larger your retirement nest egg grows. You’ll also hear how childhood money lessons still influence your decisions today—whether you realize it or not. Plus, the guys break down why FOMO and a desire to “do something” can upend a perfectly good financial plan, and how the best value a financial advisor provides may not be what you think.

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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.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian are joined by Allworth’s Chief Investment Officer Andy Stout to unpack why the latest inflation report might not be as positive as it seemed — including how a government shutdown may have warped the data. Plus, what the SEC just approved that could revolutionize how traditional investments are processed, and how Robinhood’s latest move blurs the line between gambling and investing. Later, the guys dig into the generational divide on fixing Social Security and answer your smart money questions — from multi-account withdrawal strategies to understanding bond fund risk.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian explore the hidden financial traps even the smartest, wealthiest investors fall into—often because of their own brains. From overconfidence and loss aversion to chasing performance and underestimating taxes, the co-hosts share real-life stories of multimillionaires who made emotional missteps that cost them dearly. They break down how even savvy executives, business owners, and retirement-ready couples can unintentionally sabotage long-term success. Learn how to protect yourself with smart strategies like automated rebalancing, bucket strategies, asset location, and avoiding costly tax surprises.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down a surprisingly tame inflation report that has Wall Street (and maybe the Fed) rethinking the pace of rate cuts in 2026. But don’t get too comfortable—there are warning signs in the job market that suggest the economy is cooling, not roaring. The guys explain what it all means for interest rates, your mortgage, and long-term investing strategies. Later in the show, they dive into the delicate family dynamics that can erupt when estate plans aren’t clearly communicated—think unequal inheritances, caregiver credit, and vacation home squabbles. Plus, real estate expert Michelle Sloan joins the show to walk through the pros and cons of downsizing into a condo versus staying in a traditional home. And in the Simply Money mailbag: when do alternative investments make sense, how to coordinate charitable giving without triggering higher Medicare premiums, and why your IRA investments shouldn’t change just because you plan to leave money to charity. Finally, in Brian’s Bottom Line, a financial planning playbook for high-net-worth investors in a slowing economy: diversification, liquidity, tax efficiency, and more.

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