On this episode of Simply Money presented by Allworth Financial, Bob and Brian put a $3 million retirement plan through a series of financial crash tests—from market downturns and overspending to helping adult children and losing a spouse. Plus, they lay out a five-year retirement countdown, explain how to help your kids without creating financial dependence, uncover tax opportunities that can emerge after your paycheck disappears, and reveal why checking your portfolio too often could do more harm than good.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian expose five retirement “rules of thumb” that can quickly become rules of dumb, from automatically claiming Social Security at 62 to blindly following the 4% rule or rushing to pay off a low-rate mortgage. Plus, they break down the go-go, slow-go, and no-go years of retirement, discuss when staying loyal to an employer can put your career at risk, and answer real-life questions about Roth conversions, charitable giving, permanent life insurance, and managing bonds as the national debt climbs.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian count down the 10 decisions that can make or break your retirement plan. Plus, they reveal why some “set it and forget it” investment strategies may deserve a second look, tackle your questions about tax-smart investing and helping the next generation, and explain why slowing down could save you from a costly financial mistake.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down the latest inflation numbers with Allworth Chief Investment Officer Andy Stout, what a weakening dollar and strong corporate earnings could mean for investors. Plus, they tackle new gas, grocery and supplement scams, smart Roth conversion and charitable giving strategies, and whether a cheaper first-class airline ticket is really worth it.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian unpack the seven most common financial lies we tell ourselves – from “I’ll be happy when I have more money” to “I’ll figure it out on my own.” These aren’t just small white lies; they’re deeply emotional narratives that can quietly sabotage your financial future. Whether you're navigating lifestyle creep, market timing fears, or generational silence around money, this episode helps you recognize these self-deceptions and replace them with smart, actionable advice. Plus, tips for protecting your finances through divorce, estate planning updates you might have missed, and the growing threat of elder cyber scams.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down why so many people who have done everything right—saved, invested, and built significant wealth—still don’t feel confident about their financial future. They explore the difference between passive decision-making and intentional planning, the two factors that truly move the needle, and why “hoping it all works out” can quietly derail even strong portfolios. Plus, why a financial windfall can be a risky moment if you act too quickly, how AI is starting to influence financial decisions (for better and worse), and answers to listener questions on managing concentrated stock positions, coordinating income across accounts, planning for market downturns, and making sure your financial life is prepared for the unexpected.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian tackle a question that hits differently when you’ve built real wealth: if the market dropped 20% tomorrow, what would you actually do? They walk through the emotional and mathematical realities of managing a $2–10 million portfolio, why risk tolerance and plan design don’t always align, and how shifting from accumulation to preservation changes everything. You’ll also hear strategies around sequence of returns risk, separating income streams from piles of money, and why diversification today may mean more than just a 60/40 portfolio.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian tackle a critical question for investors: what happens if the next decade of market returns doesn’t cooperate—and does your financial plan rely on strong returns just to survive? They break down how to properly stress test your retirement plan using real-world scenarios, Monte Carlo analysis, and the importance of separating must-have expenses from discretionary spending to weather any environment. Plus, they dive into the hidden complexities of restricted stock units (RSUs), including how they’re taxed, vesting schedules, and why they should be treated as a concentrated position in your portfolio. You’ll also hear strategies for protecting your retirement timing from market downturns, how to think through pension lump sum versus income decisions, and smart ways to gift money for major life events without triggering unnecessary taxes.

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On this episode of Simply Money presented by Allworth Financial, Bob and Allworth Chief Investment Officer Andy Stout break down what a weakening jobs report could mean for interest rates, why strong corporate earnings continue to support stocks, and what’s keeping pressure on the bond market. Then Brian joins Bob as they dig into Cincinnati’s “slow and steady” housing market, what retirement systems around the world can teach us, and your questions about umbrella insurance, capital gains, direct indexing, and managing a portfolio that’s become too heavy in tech.

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