Simply Money

On this episode of Simply Money presented by Allworth Financial, Bob and Brian put AI to the test, asking ChatGPT some of the most common financial planning questions—from Roth conversions and Social Security timing to concentrated stock positions and paying off a low-rate mortgage. They break down where artificial intelligence gets it right, where it falls short, and why context, personalization, and human judgment still matter when making major financial decisions.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian explore whether artificial intelligence is truly the next great investing revolution or just the latest market obsession, drawing lessons from railroads, oil, automobiles, and the dot-com boom. They also discuss why timing matters in major financial decisions, strategies for unwinding concentrated stock positions, opportunities created by low-income years, the latest trends in the Cincinnati housing market, and the most common mistakes first-generation millionaires make.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down what's fueling the market's powerful rally and why the gains are extending far beyond the Magnificent Seven. They also discuss a possible solution to Social Security's funding crisis, strategies for unwinding concentrated stock positions without creating a tax headache, when Roth conversions make sense—and when they don't—and how families can start meaningful conversations about future inheritances.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down whether Wall Street is getting ahead of itself as stocks continue climbing to new highs, with Allworth Chief Investment Officer Andy Stout weighing in on interest rates, inflation, AI's impact on jobs, and what investors should really be watching next. Plus, the cautionary tale behind NASCAR legend Kyle Busch's legal battle over indexed universal life insurance, what every investor needs to know before using life insurance as an investment strategy, answers to listener questions about Treasury Inflation-Protected Securities (TIPS), preparing financially for cognitive decline, and navigating inheritance decisions when children have dramatically different earning power. And finally, there's encouraging news on retirement savings habits as Americans quietly make a move that could significantly improve their long-term financial security.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down how financial planning has evolved from relying on pensions and predictable income streams to navigating today’s reality of managing “piles of money” through market volatility, tax complexity, and retirement uncertainty. They also discuss the hidden tax traps inside large brokerage accounts, why money tension doesn’t always disappear with wealth, and answer listener questions on family communication, charitable giving strategies, and what Social Security’s future could really mean for retirees.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down why Goldman Sachs says the AI-driven market boom may not be a bubble after all, what investors need to understand before chasing hot new ETFs and IPOs like SpaceX and OpenAI, and the growing risks of letting AI trade and spend your money. Plus, they tackle costly estate planning mistakes involving retirement account beneficiaries, explain how direct indexing can create meaningful tax savings for high-net-worth investors, and discuss smart ways to think about long-term care planning without derailing your retirement lifestyle.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down whether America’s $35 trillion national debt is a ticking time bomb for the economy and your portfolio, why more Americans are being forced into early retirement before they planned, and the biggest cybersecurity mistakes affluent families are making online. Plus, they tackle healthcare planning before Medicare, the hidden risks of Roth conversions when financial aid is on the line, and how to think through the right Social Security claiming strategy for your situation.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down the growing disconnect between how Americans feel about the economy and what the data is actually showing—as consumer sentiment falls to record lows despite strong corporate earnings and resilient spending. They also discuss the possibility of future Fed rate hikes under new Federal Reserve Chair Kevin Warsh, why the “Magnificent Seven” stocks may no longer be carrying the entire market, and how broadening earnings growth could reward truly diversified investors. Plus, they tackle one of the biggest retirement blind spots for high earners: confusing net worth with sustainable cash flow, why sudden wealth and inheritances often disappear faster than expected, strategies for drawing retirement income in the right order, what to do before a major IPO or liquidity event, and the hidden costs that can turn a dream vacation home into a financial headache.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down whether the stock market is really “about to fall off a cliff” after a high-profile economist warned the U.S. is getting dangerously close to a recession. Allworth Chief Investment Officer Andy Stout joins the show to separate scary headlines from actual economic data—covering what the bond market, housing market, labor market, and consumer confidence numbers are really saying right now.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down Nvidia’s latest jaw-dropping earnings report and what the AI boom could mean for investors, productivity, and the future of work, while also exploring the wave of high-profile IPOs coming from companies like SpaceX and OpenAI. They discuss signs of growing speculation on Wall Street, why disciplined investors should be cautious as enthusiasm ramps up again, and how wealthy families can think through long-term care planning before a crisis forces difficult decisions. Plus, they answer listener questions about estate planning after the unexpected loss of a spouse, when Roth conversions make the most sense for high earners, the hidden tax traps with private company stock options, and why used electric vehicles may quietly be one of the best values in today’s car market.

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