Simply Money

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down the modern midlife crisis—and why so many high earners are making more money than ever while feeling more trapped than ever at the same time. They discuss the rise of “golden handcuffs,” lifestyle creep, delayed retirement decisions, and the emotional realization many successful professionals face when they discover they could have stepped away years earlier. Plus, they dive into costly inherited IRA mistakes families are making under the Secure Act, strategies for managing taxes on retirement accounts, whether direct indexing is worth it for affluent investors, when municipal bonds may actually hurt your returns, and how to thoughtfully transition into retirement without losing your sense of purpose.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down why Nvidia’s earnings report could become a major report card on the entire AI infrastructure boom—and what high-net-worth investors should really be watching beneath the headlines as Wall Street starts demanding proof that massive AI spending will actually translate into long-term profits. They also discuss why your personal inflation rate in retirement may be far higher than the government’s CPI number, how overlooked estate planning strategies like the step-up in basis can potentially save families thousands in taxes, what to do after receiving a major liquidity event like the sale of a business or inheritance, whether moving to Florida for tax reasons truly makes financial sense, and why umbrella liability insurance may be one of the cheapest forms of financial protection available.

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On this episode of 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., 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 break down the key life moments when calling your financial advisor can make—or cost—you thousands. They also tackle a surprising trend: why retirees with millions saved still feel financially insecure, and how shifting from pension-style income to managing a “pile of money” has changed everything. Plus, insights from CIO Andy Stout on how tax-efficient investing strategies like tax loss harvesting and direct indexing can add real after-tax returns, and practical advice on gifting strategies, insurance gaps, and why not having a power of attorney could create major problems for your family.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down why even famous market predictors like Michael Burry shouldn’t drive your investment decisions, how volatility and bad news can actually create opportunity in a diversified portfolio, whether a vacation home is worth it, and smart strategies for handling burnout, large RMDs, real estate complexity, and co-signing risks.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down the latest inflation data as CPI comes in hotter than expected at 3.8% year-over-year—driven largely by rising energy prices tied to global conflict—and what that likely means for interest rates, the Fed’s next moves, and your portfolio strategy. They also dive into the surge in annuity sales and why “guarantees” often come with trade-offs investors don’t fully understand. Plus, a deeper conversation on what your portfolio is actually supposed to do—and why focusing only on returns can lead you astray. The show also highlights how two families with identical wealth can end up with dramatically different outcomes depending on planning decisions around RMDs, taxes, concentrated stock, and estate strategies. Finally, listener questions cover navigating retirement’s impact on marriage, whether Roth conversions still make sense if tax rates rise, and how to know when it’s time to move on from a long-time advisor.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down what a “higher for longer” rate environment means as strong job data and persistent inflation keep the Fed on hold. Allworth CIO Andy Stout explains what’s driving oil prices, why emerging markets are outperforming, and where investors should be paying attention right now. They also discuss a possible shift away from quarterly earnings reports and what it could mean for market volatility. Plus, a troubling AI deepfake scam that cost a retiree $200,000—and how to protect your family. Finally, they answer listener questions on managing a $5 million inheritance, handling RMDs tax-efficiently, protecting assets from a gambling-addicted child, and whether college is still worth the cost.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian put the last five years of stock market returns into proper perspective—breaking down why, despite volatility, disciplined investors have still seen strong long-term results, and why short-term headlines can distort reality and lead to poor decisions. They walk through recent market performance across the S&P 500, NASDAQ, small caps, and international markets, highlighting the surprising strength and broad-based nature of this rally, while also addressing the psychological challenges investors face during uncertain times.

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On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down how AI is no longer just a “big tech” story—but an economic force reshaping everything from healthcare to energy—and what that means for your investment portfolio. Plus, how to avoid lifestyle creep as your income rises, navigate delicate financial conversations with aging parents, and set healthy boundaries when family and friends come asking for financial help. And before you say yes to that vacation pitch, a clear-eyed look at whether timeshares are a smart lifestyle move—or a costly mistake you can’t easily escape.

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