Simply Money.

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.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down how to tune out scary headlines and focus on what you can actually control in your financial plan, while also showing how your tax return can reveal opportunities to lower future taxes, answering listener questions on income and capital gains, and sharing strategies to align your career, family, and charitable giving.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian explain why your portfolio may be holding up better than alarming headlines suggest, highlighting the difference between widely cited indexes like the Dow and what a truly diversified portfolio actually experiences, while also unpacking how global market shifts and proper allocation are benefiting investors. They then dive into the surprising reality that high earners often feel more financially strained due to lifestyle creep, and wrap up with listener questions on bond duration, liquidity versus market risk, the role of alternative investments, and whether reducing financial risk should come from changing your portfolio or your spending habits.See omnystudio.com/listener for privacy information.

Tonight on Simply Money presented by Allworth Financial, Bob and Brian break down the financial fallout as the war with Iran enters week three, with Allworth CIO Andy Stout joining to explain what surging oil prices, the Strait of Hormuz, and Fed uncertainty could mean for gas prices, inflation, interest rates, and your portfolio. They also cover a troubling rise in 401(k) hardship withdrawals, why private credit funds are suddenly limiting redemptions, and what that says about liquidity risk. Plus, a warning on the growing wave of financial fraud targeting older and more affluent Americans, answers to listener questions on tax risk, fund fees, portfolio risk in retirement, and rental property decisions, and a look at where retirees are moving now as cost of living and taxes reshape the old retirement playbook. See omnystudio.com/listener for privacy information.

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.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down the most expensive lies couples tell themselves about money—especially the dangerous comfort of saying “we’re fine” —and explain how a lack of communication around retirement timing, estate plans, and financial roles can cost families millions and fracture relationships. They also dig into why a single withdrawal rate like the traditional 4% rule isn’t enough, exploring sequence of returns risk, bucket strategies, flexible spending guardrails, and how small tweaks in Monte Carlo assumptions can dramatically change your plan’s success rate. Plus, Allworth’s in-house insurance expert, Jodee Deutsch, joins the show to discuss when life insurance shifts from simple protection to advanced estate and legacy planning, and how high-net-worth families can better align their wealth with their long-term goals.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian explain why the most expensive financial decisions often aren’t the ones you make — they’re the ones you avoid . They walk through real-life examples of high-net-worth families who delayed portfolio changes, tax planning, diversification, or retirement decisions, only to face bigger consequences later. The guys also break down why a “good investment” can still be a bad financial move if it increases concentration risk or limits liquidity, key questions to ask before retiring early, how to think about withdrawal strategies and portfolio drift, and one clear sign you may be overthinking your finances.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down why the financial decisions that feel boring or easy to postpone often have the biggest impact on long-term success. From overlooked beneficiary designations and withdrawal strategies to missed tax-planning windows and life risks that don’t show up in market charts, they explain how successful families can do everything “right” and still run into avoidable problems. The conversation highlights why planning for taxes, longevity, healthcare, control, and flexibility matters just as much as investment returns—especially as net worth grows—and how proactive, thoughtful decisions today can protect both your lifestyle and your legacy.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian explore what true wealth in retirement really means, from aligning your spending with your values to making smart pension choices, planning for business succession, and tackling real listener questions about emergencies, uneven expenses, and estate duties.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian explain why channeling Rip Van Winkle might be the smartest financial move you make this year, especially amid scary headlines about war, inflation, and market volatility. They walk through what would have happened if you had invested millions of dollars and then “slept” through some of the worst market moments in modern history—from the oil embargo and Black Monday to the tech bubble, the financial crisis, and COVID—and why in nearly every case, disciplined investors who stayed put woke up significantly wealthier.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian explain why the first five years of retirement can make or break even a $5 million portfolio. They break down sequence of returns risk, walk through real-world examples of how early market drops can permanently impact your plan, and share strategies like liquidity buckets and disciplined rebalancing to protect your future. Plus, common 401(k) mistakes successful investors make, how to prevent concentrated stock from quietly dominating your portfolio, what to do if your financial life is split across multiple advisors, and how to safeguard your finances if a spouse becomes cognitively impaired.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down the stock market volatility tied to escalating tensions in the Middle East and the critical Strait of Hormuz, where roughly 20% of global oil flows, looking back at the 1973 OPEC oil embargo, stagflation, and how markets have historically responded to geopolitical shocks. They also cover State Farm’s historic $5 billion dividend payout to auto policyholders, Google’s bold move to issue a 100-year bond as a long-term AI confidence play, and the reality of potential Social Security benefit reductions in the early 2030s. Finally, they wrap with listener questions on adjusting stock allocations amid global conflict, calculating emergency cash when income fluctuates, and whether to lock in gains early in retirement or simply rebalance and stay disciplined.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down the market reaction to escalating conflict in the Middle East and explain why, despite headlines that feel different every time, markets price expected earnings—not emotion. They walk through the psychological biases that can push even experienced, high-net-worth investors into costly mistakes and outline what would truly signal a structural market shift. Then, they uncover a hidden tax bomb that may be lurking in your brokerage account—especially if you hold highly appreciated ETFs or concentrated company stock—and share smart, multi-year strategies to manage capital gains before they manage you.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down how investors should interpret the major geopolitical conflict unfolding in Iran and the broader Middle East. Allworth Chief Investment Officer Andy Stout joins the show to explain how markets are pricing in the uncertainty, why the Strait of Hormuz matters so much to global oil supply, and what a “worst-case” energy disruption could mean for inflation, Fed policy, and your portfolio. See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian ask a powerful retirement question: if work vanished tomorrow and money wasn’t a concern, who would you be? They explore why affluent professionals often fear losing purpose more than running out of money, how identity and spending shift after retirement, and why “test-driving” your next chapter may be the smartest move you make. Plus, what Americans say they’ll do with their tax refunds — and why reality will likely say otherwise.See omnystudio.com/listener for privacy information.

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 portfolioSee omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian unpack why the rise of AI company Anthropic is moving markets—even though you can’t invest in it—and what that means for portfolios that may already be heavily exposed to tech. The conversation then shifts to retirement realities, including the often-underestimated cost of healthcare and the critical need to plan for cognitive decline before it becomes a crisis. They also highlight a troubling AI deepfake scam that cost an 82-year-old woman $200,000 and share practical steps to protect your family, while answering listener questions on Roth conversions, managing excess cash, and whether the AI boom is just another bubble in the making. See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down the latest Social Security shortfall projections and what they really mean for your retirement plan, discuss whether new hedge-fund-style ETFs add real diversification or just complexity, explore how to stay relevant in an AI-driven workplace, and answer listener questions on portfolio risk, diversification, and protecting your financial information in today’s digital world.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down the Supreme Court’s 6–3 ruling against a major part of President Trump’s global tariff strategy and what it means for the markets, the $133 billion already collected, and your portfolio, with insight from Allworth Chief Investment Officer Andy Stout in Cincinnati. They also dive into the growing push to add private equity to 401(k)s, the risks of over-optimizing your financial plan while ignoring big lifestyle decisions, listener questions on retirement income sustainability, inherited money anxiety, and exiting a business, and a controversial proposal to eliminate property taxes in Ohio — all with a focus on helping high-net-worth families tune out political noise and stay grounded in long-term fundamentals.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down the $2 million retirement illusion — why that number used to mean financial independence, but today can leave some families feeling secure and others deeply uncertain. They explain how inflation, taxes, lifestyle creep, supporting adult children and aging parents, and market volatility all impact what $2 million can realistically generate, why spending is the biggest lever in retirement success, and how the way your assets are structured (pre-tax vs. Roth vs. taxable) can dramatically change your outcome. See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian explain why your cash hoard might be quietly costing you millions over time, even as the S&P 500 has delivered a 330% total return over the past decade with dividends reinvested. They break down the real risks of sitting on 15–30% in cash, why waiting for the “perfect” market pullback often backfires, and how to determine the right amount of liquidity within a comprehensive financial plan. Plus, smart strategies around tax extensions, Roth conversions before RMDs begin, concentrated stock positions, and the critical three-year runway before selling a business.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian explore a simple phrase that could mean the difference between financial freedom and struggle: “the sooner the better.” They unpack new data around Gen X’s looming retirement crisis and what it means to be the first generation largely retiring without pensions. Then, they dive into a compelling new study showing how saving—not spending—could be the true key to financial happiness. Plus, career expert Julie Bauke joins to dissect “the executive dilemma”—when a promotion might not actually be the best next move. Finally, Bob and Brian answer real listener questions on managing capital gains, tapping into dividends, and planning for long-term care.See omnystudio.com/listener for privacy information.

On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down the most expensive lies couples tell themselves about money—especially the dangerous comfort of saying “we’re fine” —and explain how a lack of communication around retirement timing, estate plans, and financial roles can cost families millions and fracture relationships. They also dig into why a single withdrawal rate like the traditional 4% rule isn’t enough, exploring sequence of returns risk, bucket strategies, flexible spending guardrails, and how small tweaks in Monte Carlo assumptions can dramatically change your plan’s success rate. Plus, Allworth’s in-house insurance expert, Jodee Deutsch, joins the show to discuss when life insurance shifts from simple protection to advanced estate and legacy planning, and how high-net-worth families can better align their wealth with their long-term goals.See omnystudio.com/listener for privacy information.

See omnystudio.com/listener for privacy information.