Simply Money by Allworth Financial
The Best of Simply Money podcast covers all topics that affect your wallet: insight into business news, consumer finance, and retirement planning. The show is a weekly collection of segments which originally aired on 55KRC.
AI Is Booming. But Will You Invest in the Right Companies?
On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down Anthropic's highly anticipated IPO, the eye-popping revenue numbers, and why investors should be cautious about chasing the AI hype. Plus, they examine silver's wild price swings, explain when a living trust makes more sense than a simple will, and answer listener questions about concentrated company stock and minimizing taxes on an inherited IRA. They also share why communicating your estate planning wishes could be just as important as the documents themselves.
The Retirement Planning Gap—and How to Close It
On this episode of Simply Money presented by Allworth Financial, Bob and Brian reveal the surprising gap between thinking about retirement and actually planning for it, explain why paying taxes now could save you thousands later, and welcome Allworth estate planning expert Paul Schwartz to uncover common estate planning mistakes. Plus, smart strategies for selling a vacation home, making the most of tax losses, gifting appreciated stock to your kids, and the surprising role money plays in keeping relationships together.
Bull vs. Bear Markets: Why Staying Invested Matters
On this episode of Simply Money presented by Allworth Financial, Bob and Brian reveal what decades of bull and bear markets can teach investors about building long-term wealth, explain why some new ETFs look more like gambling than investing, and discuss the executive dilemma of whether a bigger paycheck and title are worth the trade-offs. Plus, smart strategies for reducing capital gains taxes, donating appreciated stock to charity, knowing when you no longer need life insurance, and why bonds deserve another look.
The Investing Mistake That Can Wreck a Portfolio
On this episode of Simply Money presented by Allworth Financial, Bob and Brian explain why even great companies can become terrible investments, what earnings season could reveal about today's AI boom, and why some high earners are rethinking the advice to max out their 401(k)s. Plus, a financial makeover for empty nesters, smart ways to help adult children financially, what you should expect from a wealth advisor, and why planning for retirement means more than just managing your money.
The Most Expensive Money Mistakes Successful People Make
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.
Can Your $3 Million Retirement Survive a Crash Test?
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.
The 10 Decisions That Can Make or Break Your Retirement
On this episode of Simply Money, Bob and Brian count down the 10 decisions that can make or break your retirement plan. Plus, they reveal why some “set it and forget it” investment strategies may deserve a second look, tackle your questions about tax-smart investing and helping the next generation, and explain why slowing down could save you from a costly financial mistake.
Are You Really as Wealthy as Your Net Worth Says?
On this episode of Simply Money presented by Allworth Financial, Bob and Brian explain why your net worth may not tell the full story of your financial health, how to identify your most valuable asset at every stage of life, and why forgotten 401(k)s deserve a closer look. Plus, they tackle retirement spending, helping your kids financially, concentrated stock positions, and when it’s time to rethink an old life insurance policy.
The Most Dangerous Years of Retirement
On this episode of Simply Money, Bob and Brian explain why the first five years of retirement can make or break your financial plan, how a rising market can quietly increase the risk in your portfolio, and why having enough money to buy something doesn’t necessarily mean you should. Plus, they tackle tax-loss harvesting pitfalls, managing concentrated company stock, and why today’s mortgage rates shouldn’t be the only factor driving your decision to buy a home.
Why More Money Doesn’t Always Mean More Security
On this episode of Simply Money, Bob and Brian explain why having more money doesn’t always mean feeling more financially secure, reveal the overlooked portfolio number that could trigger a major tax bill, and discuss why some retirees may be waiting too long to enjoy the wealth they’ve built. Plus, how to navigate wealth differences with friends, plan for valuable collectibles, and recognize three phrases that should immediately put you on alert for a scam.
The 10 Decisions That Can Make or Break Your Retirement
On this episode of Simply Money, Bob and Brian count down the 10 decisions that can make or break your retirement plan. Plus, they reveal why some “set it and forget it” investment strategies may deserve a second look, tackle your questions about tax-smart investing and helping the next generation, and explain why slowing down could save you from a costly financial mistake.
The 10-Year Test Your Financial Plan Needs to Pass
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 c...
How to Protect Your Wealth From Mistakes You Can't Undo
On this episode of Simply Money, Bob and Brian explain why today's market bubbles may be smaller—and less dangerous—than the ones investors remember from the dot-com era and the financial crisis. They also discuss when alternative investments like private equity actually make sense, sit down with Allworth Senior Estate Planning Specialist Paul Schwarz to share strategies for preparing the next generation for one of the largest wealth transfers in history, and answer listener questions on building a lasting family legacy and protecting generational wealth.
The Smart Money Moves That Matter at Every Age
On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down the key financial moves that matter most in every decade of your life—from building wealth in your 20s and 30s to protecting it in your 40s and preparing for retirement in your 50s and beyond. They also explain how hidden tax traps can develop inside brokerage accounts, answer listener questions on estate planning, retirement tax strategies, and umbrella insurance, and sit down with Allworth's insurance expert to discuss when long-term care insurance actually makes sense. Plus, Bob shares his perspective on whether homeownership is...
The Stock Market's Next Test—and How Much Cash You Really Need
On this episode of Simply Money presented by Allworth Financial, Bob and Brian explain why this earnings season could be one of the biggest tests for the stock market in years—and what investors should really be watching beyond the headlines. They also discuss how much cash you actually need, why too much liquidity can quietly hurt your long-term wealth, practical ways to protect your finances from growing cybersecurity threats, and answer listener questions on helping adult children fairly, qualified charitable distributions, stock option taxes, and tax-smart investing strategies.
The Retirement Mistake No Financial Plan Can Solve
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...
What the Market Is Really Telling You—and Why Retirement Spending Is So Hard
On this episode of Simply Money presented by Allworth Financial, Bob and Brian explain what the Dow, S&P 500, and NASDAQ really measure—and why understanding the differences can make you a more informed investor. They also discuss why so many retirees struggle to shift from saving to spending, get the latest on the Greater Cincinnati housing market, and answer listener questions on making a $1 million 401(k) last, inherited stock, and when a trust may make more sense than a simple will.
The 7 Financial Lies That Could Be Costing You Millions
On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down the seven financial lies we tell ourselves—from believing more money will finally make us happy to thinking we can time the market, save later, or figure everything out on our own. They also discuss the financial realities of divorce, why cybercriminals are increasingly targeting seniors and their life savings, how to prepare your spouse to take over the family finances if needed, and critical estate planning mistakes that can create major headaches for your heirs. Plus, answers to listener questions on emergency funds, co...
The Hidden Risk in Your “Diversified” Portfolio
On this episode of Simply Money presented by Allworth Financial, Bob and Brian explain why many investors who think they’re diversified may actually have far more exposure to AI and semiconductor stocks than they realize, how concentration risk has shown up throughout market history, and what wealthy investors can do to protect against it. They also break down the recent pullback in private credit funds, the dangers of relying on active managers to pick the next market winners, why your portfolio’s purpose matters more than its returns, and answer listener questions on direct indexing, family business inheritance plan...
The Biggest Threat to Your Retirement Isn't the Stock Market
On this episode of Simply Money presented by Allworth Financial, Bob and Brian explain why the biggest risk to your retirement may have nothing to do with the stock market. From rising healthcare costs and long-term care planning to selling a business and navigating looming tax challenges, they cover the financial decisions that can have the biggest impact on your future. Plus, former Cleveland Fed President Dr. Loretta Mester joins the show to share her perspective on the Federal Reserve's latest decision and what investors should be watching next.
Are You Really Diversified? Plus Life Insurance Gaps and Protecting Family Wealth
On this episode of Simply Money presented by Allworth Financial, Bob and Brian explain what true diversification looks like in today's market—and why owning more investments doesn't always reduce risk. They also discuss a proposal that could bring private equity, crypto, and other alternative investments into 401(k) plans, and whether highly compensated employees have enough life and disability insurance coverage.
Plus, they answer listener questions on navigating different retirement timelines, protecting family wealth from divorce risk, tax planning after moving to Florida, and preparing to sell a closely held business.
Is AI the Next Investing Revolution—or the Next Dot-Com Bubble?
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.
The One Thing That Can Wreck Your Retirement—Even With Millions Saved
On this episode of Simply Money presented by Allworth Financial, Bob and Brian explain why having millions saved for retirement still doesn’t guarantee financial freedom—and how many high earners unknowingly sabotage their own retirement plans through lifestyle creep, unchecked spending, and poor cash-flow awareness. They also discuss the psychological dangers of sudden wealth and inheritances, why some people lose massive windfalls within just a few years, how to thoughtfully manage newly inherited money, and the smartest order to draw income from pensions, Social Security, deferred comp, and investment accounts in retirement.
Plus, they break down what...
How to Turn Financial Success Into Personal Freedom
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...
The 5 Key Times to Call Your Financial Advisor
On this episode of Simply Money, 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...
Does Your Financial Plan Depend on a “Good” Market Decade?
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 tre...
Market Noise, Portfolio Strategy, and Smarter Investing Moves
On this episode of Simply Money, 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.
Diversification Matters: What the Latest Market Rally Is Really Telling Investors
On this episode of Simply Money, 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.
The Biggest Stock Market Mistakes Investors Still Make
On this episode of Simply Money, Bob and Brian break down the biggest stock market mistakes investors still make—even as more Americans than ever are participating in the market. They discuss the shift from pensions to 401(k)s, why younger investors may be taking too little risk, and how to properly align your portfolio with your financial plan instead of your age.
Plus, a deep dive into the Rule of 55 and how it can help unlock early retirement, smart strategies for handling required minimum distributions if you don’t need the income, and how life insurance can...
What Two Trading Days Exposed About Investor Behavior
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.
What Smart Investors Are Doing With Their Portfolios Right Now
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.
The Hidden Gap Between Building Wealth and Feeling Secure
On this episode of Simply Money, 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 c...
Why Your Portfolio Doesn’t Match the Headlines (And the Hidden Cost of Lifestyle Creep)
On this episode of Simply Money, Bob and Brian break down why your portfolio may not be falling—even when scary headlines suggest markets are in turmoil. They explain the disconnect between media narratives and real investor experience, including why the Dow’s dramatic point swings don’t tell the full story and how proper diversification—especially with international stocks and small cap value—has quietly supported portfolios in 2026.
Plus, a surprising (and alarming) trend: high-income households earning $300K–$500K are more likely to feel “paycheck to paycheck” than those earning far less. Bob and Brian unpack the real culprit...
The Hidden Risks That Can Derail Your Financial Plan
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...
What Oil Shocks Mean for Your Investment Portfolio
On this episode of Simply Money, 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.
Plus, they answer 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.
What Would You Actually Do in a 20% Market Drop?
On this episode of Simply Money, 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. Plus, the guys explain why bonds weren’t the “safe...
The “We’re Fine” Trap: Withdrawal Rates, Wealth Gaps & Planning That Actually Works
On this episode of Simply Money, 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, j...
Big Wealth, Small Mistakes: The Decisions That Matter Most
On this episode of Simply Money, 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 protec...
Does a Strong January Really Matter? Rethinking Bonds, Risk, and Retirement Planning
On this episode of Simply Money presented by Allworth Financial, Bob and Brian break down whether a strong January really sets the tone for the rest of the market. They explain why diversification is resurfacing as international stocks and small caps outperform, dig into why the world’s largest asset manager says bonds may no longer protect portfolios the way investors expect, and share smarter ways to manage risk and income in retirement, including shorter-duration bonds and buffered strategies.
The show also tackles real planning decisions around selling appreciated investments, evaluating active managers, estate planning for blended fa...
The Financial Blind Spots High-Net-Worth Investors Can’t Ignore
On this week’s Best of Simply Money podcast, Bob and Brian issue a critical warning for anyone who’s never vetted their financial advisor—breaking down a real-life fraud case and how to protect yourself. They unpack whether gold belongs in your portfolio, reveal the hidden risks of neglected 401(k)s, and explain how to make them work harder for high-net-worth investors. Plus, smart listener questions on helping kids with a home down payment, guarding against early-retirement market drops, and unwinding a concentrated stock position without triggering a massive tax bill.
