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. See omnystudio.com/listener for privacy information.

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.See omnystudio.com/listener for privacy information.

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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.See omnystudio.com/listener for privacy information.

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.See omnystudio.com/listener for privacy information.

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.See omnystudio.com/listener for privacy information.

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. See omnystudio.com/listener for privacy information.

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. See omnystudio.com/listener for privacy information.

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. See omnystudio.com/listener for privacy information.

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.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down three powerful—and very different—voices shaping investor sentiment right now, from Warren Buffett’s warning that markets are behaving more like a casino than a place for disciplined investing, to Jamie Dimon’s concerns that inflation and interest rates could stay higher for longer and create new hurdles for growth, to Elon Musk’s bold claim that saving for retirement may one day be unnecessary in an AI-driven world. Along the way, they unpack what all of this means for long-term investors, why short-term trading strategies can quietly derail even smart portfolios, and how to separate meaningful financial insight from attention-grabbing noise when making big decisions about your money.See omnystudio.com/listener for privacy information.

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. See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down why stocks just had their best month in five years while gold is plunging—despite global conflict—and what that signals about investor sentiment, inflation expectations, and where markets may head next. They also uncover a report revealing over $160 million in missed or underpaid Social Security benefits impacting thousands of retirees, discuss the real risks of letting AI make financial decisions on your behalf, and answer listener questions on Roth conversions, charitable giving strategies, and whether real estate still deserves a place in a high-net-worth portfolio.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down the hidden danger in today’s markets: not panic—but complacency. While headlines are filled with war, inflation concerns, and uncertainty, investors seem unfazed—and that can create its own set of risks. They walk through real-life scenarios of retirees staying too heavily invested in equities, “set it and forget it” millionaires ignoring portfolio drift, and couples making major purchases without proper planning—highlighting how overconfidence and lack of discipline can quietly derail even strong financial plans.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down how four big tech companies moved the market in minutes after earnings, why strong cloud growth continues to power the economy, what a steady GDP report really says about where we’re headed, and how big life decisions—from age-gap marriages to AI in the workplace—can impact your financial plan.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down the Fed’s decision to hold interest rates steady and what it really signals for investors, why the old “sell in May and go away” strategy can do more harm than good, and the hidden risks in chasing market trends—from short squeezes to speculative betting markets—while also answering listener questions on Roth conversions, pre-tax retirement strategies, and navigating a surprise business buyout offer. See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down three conflicting market predictions making headlines right now—and why reacting to any of them could derail your long-term plan—while also diving into the dangers of turning your 401(k) into a betting platform, whether a “too balanced” portfolio could actually hurt your growth, how appraisal gaps can impact what you really pay for a home, and smart strategies for high-net-worth investors including direct indexing, managing large IRA balances, and planning for long-term care without over-insuring.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down what really drives the markets—cutting through the noise of scary headlines to focus on corporate earnings, recession risk, and the health of the consumer—while also exploring the impact of stock buybacks like Netflix’s massive program, how your identity can complicate retirement more than your finances, and smart strategies for managing concentrated stock, charitable giving, and building a sustainable retirement plan.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down a bold—and controversial—investment strategy suggesting nearly half your portfolio belong in gold, commodities, and even Bitcoin, with zero allocation to bonds. They dig into why some global strategists are losing faith in traditional portfolio construction, what’s really driving the fear around inflation and government debt, and why abandoning bonds altogether could create more volatility—not less. Plus, a reality check on cryptocurrency as a true currency, including what happened when El Salvador made Bitcoin legal tender—and why it hasn’t delivered on its promises. Finally, they explain how smart bond management—like adjusting duration and laddering maturities—can still play a critical role in building a resilient, income-producing portfolio.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian separate fact from fiction when it comes to the latest “stock market bubble” headlines. They also walk through the real-world decisions around unwinding rental properties, from 1031 exchanges to depreciation recapture, plus practical home maintenance tips that can protect one of your largest assets, and answers to listener questions on backdoor Roth strategies, inherited IRA withdrawal rules, and balancing charitable giving with family goals.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down the implications of Fed chair nominee Kevin Warsh’s confirmation hearing with insights from former Cleveland Fed President Dr. Loretta Mester, explaining why Fed independence matters and how decisions are really made. They also explore new data showing declining retirement confidence as rising healthcare, travel, and housing costs weigh on retirees, along with practical guidance on building a plan that accounts for those realities. Plus they tackle listener questions by offering solutions for managing retirement cash flow when assets are tied up in private equity, investing excess income tax-efficiently after maxing out retirement accounts, and reevaluating municipal bond strategies as income changes.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian explain why the market rebounded sharply despite global conflict, highlighting how one company—Micron Technology—is driving a surprising share of earnings growth expectations and what that means for diversification and long-term investors. They also discuss the risks of relying on headline-making company CEOs, answer listener questions on direct indexing, tax planning in retirement, and concentrated stock positions, and wrap up with smart, flexible strategies for funding grandchildren’s education using tools like 529 plans.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down why markets can surge to record highs even as geopolitical tensions with Iran create ongoing uncertainty, and what that means for investors trying to time the “all clear.” They also dive into the risks of chasing hype after a sneaker company’s AI-fueled stock spike and crash, and the broader lessons for anyone tempted by momentum trades. Plus, practical advice on managing complex financial decisions—from reviewing life insurance and executing Roth conversions to maximizing charitable giving strategies. And finally, a discussion on new Social Security proposals that could impact high earners down the road. See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down why the market so often defies logic—and discuss why a so-called “WTF indicator” is really a reminder that trying to predict short-term moves is a losing game, even for the smartest investors. They explain why headlines rarely match market performance, how forward-looking expectations drive returns, and why sitting on the sidelines can cost you more than volatility ever will.See omnystudio.com/listener for privacy information.

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.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down what big bank earnings are revealing about the economy and why it matters for your portfolio, explore how record-low U.S. birthrates could impact Social Security and long-term financial planning, and answer listener questions on portfolio risk, deferred compensation strategies, estate organization, and whether to pay off a low-interest mortgage or stay invested.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down the latest inflation spike fueled by rising energy prices and what it means for markets, interest rates, and your portfolio—while Allworth CIO Andy Stout explains why core inflation remains more stable beneath the surface. They also cover a local Ponzi scheme that led to prison time and the key red flags investors can’t afford to ignore, plus smart strategies for selling a business, choosing between municipal and taxable bonds, and where private investments fit for high-net-worth portfolios. Finally, they highlight common tax-season regrets—and how proactive planning now can save you thousands next year.See omnystudio.com/listener for privacy information.

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.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian challenge the traditional idea of retirement, exploring why having enough money isn’t the same as having a fulfilling plan for what comes next. Inspired by a powerful real-life story, they discuss “purpose risk,” the dangers of tying your identity solely to your career, and why true financial success is about creating optionality in your life—not just building wealth. They also break down how to turn your savings into a tax-efficient income stream, why rules like the 4% guideline can fall short, how to manage risk and cash flow in retirement, and why your “forever home” might not be as permanent as you think.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down how just two trading days over the past year could have dramatically impacted your portfolio—and why trying to time the market based on fear can cost you millions over time. They also cover the risks of having multiple old 401(k)s, smart strategies for Roth conversions and tax-efficient charitable giving, how to approach estate planning conversations with aging parents, the importance of pre-planning end-of-life decisions, and when advanced strategies like direct indexing actually make sense for higher-net-worth investors. See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down a potential inflation spike driven by surging oil prices and what it means for Fed rate cuts, while also explaining why your retirement “number” might be completely wrong, how sudden wealth can quietly destroy your finances, and answering listener questions on investing cash, gifting strategies, and making sure your plan actually lasts as long as you do.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down the biggest investing mistakes they know happened during a volatile week in the markets—from chasing scary geopolitical headlines and trying to time sector moves like gold and energy, to overreacting to massive daily swings and sitting on cash waiting to “buy the dip.” They explain why the market often prices in news before you can act, how missing just a handful of the best days can derail long-term returns, and why doing nothing can sometimes be the most disciplined—and profitable—move. Plus, they share what smart investors actually did this week, including rebalancing, tax loss harvesting, and revisiting their financial plans to stay on track.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down why the market isn’t reacting to headlines—but pricing in what comes next—and how indicators like the VIX can help high-net-worth investors better understand volatility, risk pricing, and opportunity. They also dive into Apple at 50 and whether it still deserves a place in your portfolio today, how to handle financial pressure from family and friends without damaging relationships, smart strategies around tax loss harvesting and Roth conversions, and what many investors misunderstand about target date funds.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian explain why reacting to headlines and trying to time market sectors—from energy to tech to gold—can derail your long-term plan, especially in fast-moving geopolitical environments, while also breaking down a push to bring private equity and crypto into 401(k)s, what to do with a major inheritance, how to coordinate deferred comp, smart charitable giving strategies, what’s really happening in Cincinnati’s spring housing market, and why your tax return holds key planning opportunities.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down why investors aren’t panicking despite rising geopolitical tensions, what that means for your portfolio, and how to prepare for volatility with smart planning, liquidity, and tax strategies—plus insights on life insurance decisions, concentrated stock risk, selling a business, Roth conversions, and why having proactive family conversations about long-term care matters more than ever.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down the recent market volatility and why corrections are a normal part of investing, with insight from CIO Andy Stout on what history tells us, where global markets stand, and what his recession scorecard is signaling. They also discuss the looming Social Security shortfall and lack of action in Washington, the growing $1 trillion impact of unpaid caregiving on families, and answer listener questions on direct indexing, trusts, and charitable strategies—plus a look at teens getting early access to investing and what that means for financial education.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian take a deep dive into one of the most dangerous phrases in investing—“this time is different”—and why history shows that investor behavior often repeats itself, even when markets, technology, and opportunities evolve. They walk through a century of market cycles, from the optimism of the Roaring 1920s and the devastation of the Great Depression, to the dot-com bubble, the housing crash of 2008, and the more recent frenzy around SPACs, meme stocks, and crypto. Along the way, they share personal stories from their early careers, highlighting how real experience through a full market cycle shapes smarter investors, and why understanding behavioral biases like recency bias and overconfidence is critical—especially for those managing significant wealth.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down why recession headlines don’t tell the full story, the hidden risks in private credit and alternative investments, and why many high-net-worth retirees are actually saving too much instead of enjoying their money—plus answers on insurance, taxes, and helping your kids financially.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down how to turn market volatility into opportunity—using smart strategies like tax loss harvesting and direct indexing to play both defense and offense—while also tackling the reality that many retirees don’t get to “call their shot,” how to prepare for an earlier-than-planned exit from the workforce, the latest scams targeting your money, and practical advice on everything from cash reserves to navigating family financial dynamics. See omnystudio.com/listener for privacy information.

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.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down why this latest market “correction” is yet another reminder that trying to time short-term moves is a fool’s errand, as headline-driven volatility—from geopolitical tensions to sudden reversals in futures—continues to whipsaw investors. The conversation then pivots to a major fiduciary rule change out of Texas that could make it harder to identify trustworthy financial advice, especially as trillions are expected to roll from 401(k)s to IRAs in the coming years. Plus, they tackle listener questions on trimming concentrated stock positions, avoiding second-guessing after rebalancing, and what to do if you’ve been sitting on a large pile of cash waiting for the “right time” to invest.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian explain why the real danger to your wealth right now isn’t inflation itself, but how investors react to it—often by getting overly defensive, raising cash, and pulling back from growth, which can quietly erode purchasing power over time. Using lessons from the 1970s and real-world portfolio examples, they highlight how inflation is cumulative, why “playing it safe” can backfire, and how even high-net-worth investors risk compressing their future if their portfolios aren’t built to outpace rising costs. They also share why disciplined allocation, proper use of cash buckets, and stress-testing your plan during good markets are key to staying on track for the long term.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian challenge the traditional idea of retirement, exploring why having enough money isn’t the same as having a fulfilling plan for what comes next. Inspired by a powerful real-life story, they discuss “purpose risk,” the dangers of tying your identity solely to your career, and why true financial success is about creating optionality in your life—not just building wealth. They also break down how to turn your savings into a tax-efficient income stream, why rules like the 4% guideline can fall short, how to manage risk and cash flow in retirement, and why your “forever home” might not be as permanent as you think.See omnystudio.com/listener for privacy information.