On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down why the financial decisions that feel boring or easy to postpone often have the biggest impact on long-term success. From overlooked beneficiary designations and withdrawal strategies to missed tax-planning windows and life risks that don’t show up in market charts, they explain how successful families can do everything “right” and still run into avoidable problems. The conversation highlights why planning for taxes, longevity, healthcare, control, and flexibility matters just as much as investment returns—especially as net worth grows—and how proactive, thoughtful decisions today can protect both your lifestyle and your legacy.

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On this episode of Simply Money presented by Allworth Financial, Brian unpacks a major market milestone as the Dow crosses 50,000, with Allworth CIO Andy Stout explaining what disciplined investors should do amid AI-driven volatility, valuation concerns, and mixed economic signals. They also dig into Bitcoin’s sharp drop and rebound, discussing whether crypto belongs in a real financial plan, then shift to the highly emotional decision of downsizing your home — covering taxes, lifestyle tradeoffs, and common mistakes retirees make. The show wraps with a powerful look at how small choices today can dramatically shape retirement outcomes years down the road.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian tackle the best—and worst—money advice you’re likely to hear at a Super Bowl party and explain why tips from “successful” friends, doctors, executives, or business owners can still lead you astray. They break down common myths like ditching bonds entirely, never selling company stock because of taxes, assuming your CPA is handling long-term planning, believing you’ll automatically be in a lower tax bracket in retirement, and thinking your kids will “figure it out” when they inherit your wealth. Along the way, they share smarter alternatives using tools like buffered ETFs, direct indexing, tax-loss harvesting, proactive tax planning, and intentional family conversations so party chatter doesn’t end up calling the plays in your real financial plan.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian explain what the recent AI and Magnificent Seven pullback really means for investors, why volatility is normal when stocks are priced for perfection, and why diversification matters more than ever. They dig into the often-overlooked threat of rising healthcare costs in retirement, including Medicare premiums, IRMAA surcharges, HSAs, and Roth planning. They also break down where AI can help with financial decisions and where you still need a human in the room. The show answers listener questions on inherited IRAs, surprise capital gains in taxable mutual funds, and rebalancing during volatile markets, and closes with a candid look at financial secrecy in relationships and why transparency may be one of the smartest money moves you can make.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down why many investors who feel diversified may be taking on far more risk than they realize, as a small group of mega-cap tech stocks now drive a disproportionate share of market returns. They explain how popular index and total market funds can quietly become concentrated, especially for investors nearing retirement, and why volatility hurts more when you’re transitioning from saving to spending. Bob and Brian also share practical ways to think about true diversification—looking beyond cap-weighted U.S. stocks to international equities, small-cap value, private investments, and buffered ETF strategies—so your portfolio supports your retirement lifestyle instead of putting it at risk.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down whether a strong January really sets the tone for the rest of the market. They explain why diversification is resurfacing as international stocks and small caps outperform, dig into why the world’s largest asset manager says bonds may no longer protect portfolios the way investors expect, and share smarter ways to manage risk and income in retirement, including shorter-duration bonds and buffered strategies. The show also tackles real planning decisions around selling appreciated investments, evaluating active managers, estate planning for blended families, and why proactive conversations around aging parents can prevent financial and emotional chaos later on.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian explore a surprising truth: being intelligent doesn’t protect you from making poor financial decisions. In fact, sometimes it makes things worse. They uncover the hidden forces—confirmation bias, inertia, overconfidence—that trip up even the savviest investors, especially those who’ve accumulated real wealth. Learn why building systems and seeking second opinions is essential if you’re in the $2-10 million net worth range. Plus, they examine the looming retirement fears of Generation X, including healthcare costs and long-term care.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down why retirement today looks nothing like it did for previous generations. From skyrocketing healthcare costs and longer lifespans to new tax law changes and the growing complexity of managing large retirement accounts, they explore how to truly prepare for this new era. They explain why many retirees are still working—not out of necessity, but by choice—and why high-net-worth families need to be especially cautious about rollovers and planning for long-term care. Plus, how psychological hurdles might be the biggest retirement challenge of all.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian dig into a major shakeup at the Federal Reserve as a new nominee emerges to potentially lead the Fed—and why that news sent shockwaves through gold, silver, crypto, and currency markets. Allworth Chief Investment Officer Andy Stout joins the show to break down what a Kevin Warsh–led Fed could mean for interest rates, the Fed’s massive balance sheet, and long-term investors trying to navigate volatility. The guys also tackle growing concerns about a potential “lost decade” for stock returns, what history tells us about flat markets, and how smart planning—not panic—helps protect your retirement. Plus, they explore when real estate becomes too much of a good thing, answer nuanced listener questions around taxes, trusts, and retirement income strategies, and close with a timely Groundhog Day reminder on why repeating the same financial habits can quietly hold you back

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