On this episode of Simply Money presented by Allworth Financial, Bob and Brian play a financial game of “Would You Rather?” to tackle some of retirement’s biggest tradeoffs. Plus, they reveal the estate planning detail even wealthy families can overlook, explain why waiting too long to enjoy your money can be a retirement mistake, and answer listener questions about Roth conversions, concentrated stock, and planning when you don’t know when you’ll retire.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down the latest inflation numbers and what they could mean for the Fed, reveal why reading the fine print before buying a hot IPO matters, and debate whether your home should really be considered an investment. Plus, they tackle your questions about retirement savings, highly appreciated investments and gifting to your kids, and share ways to fight back against relentless spam calls.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian reveal the costly financial mistakes even successful investors can make, from concentrated investments and poor tax planning to holding too much cash and lifestyle creep. Plus, they explore the life decisions that can shape your wealth, explain when it’s time to review old insurance policies, and answer retirement questions about Roth conversions, Social Security, and leaving an inheritance your heirs can handle.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian look at whether higher Treasury yields should change your investment strategy, the growing concentration of the S&P 500, and why business owners need to start planning years before a sale. Plus, they tackle helping adult children buy a home, retiring years before your spouse, gifting appreciated stock, and when to claim Social Security.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian explain why election-year anxiety shouldn’t drive your investment decisions. They dig into decades of market history showing how stocks have performed under both Republican and Democratic leadership, why presidents often get too much credit—or blame—for market returns, and why your long-term financial plan should matter far more than who controls Washington.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian reveal how inflation quietly erodes your purchasing power—and why playing it too safe in retirement can create risks of its own. Plus, they look at what Home Depot’s remarkable long-term run can teach investors about chasing today’s hottest stocks, explain why too much loyalty to your employer could hurt your career, and answer questions about umbrella insurance, charitable giving, and helping adult kids invest without jeopardizing your own retirement.

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On this episode of Simply Money, Bob and Brian crash-test a $3 million retirement plan against market drops, overspending, family gifts, and an early death. Plus, they lay out a five-year retirement countdown, explain how to help your kids without creating financial problems, and discuss smart tax moves that could open up once the paycheck stops.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down the hype and risks surrounding a potential blockbuster Anthropic IPO, why some retirees may actually be too reluctant to spend their savings, and why your portfolio’s purpose should matter more than chasing returns. Plus, they tackle your questions on early retirement, leaving money to your kids, and what soaring diesel prices could mean for inflation.

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