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The Best-of Simply Money is a weekly collection of the best segments that originally aired for the daily show on 55KRC. We cover all topics that affect your wallet: insight into business news, consumer finance, and retirement planning.
170 Episodes
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On this week’s Best of Simply Money podcast, Bob and Brian take a deep dive into what really happened in 2025 — and why the investing fundamentals they shared all year long held up once again. From President Trump’s return and a new wave of tariffs, to a Federal Reserve caught between inflation and politics, to a stock market rally that rewarded patient investors — they told you what to expect, and they were right. Hear what mattered most, what moved the markets, and what lessons investors should take into 2026. Plus, the rise of real financial resolutions, how to measure if your money actually did its job this year, and your smart money questions answered.
On this week’s Best of Simply Money podcast, 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.
On this week’s Best of Simply Money podcast, Bob and Brian explore whether we’re living through another tech bubble — this time fueled by artificial intelligence. Is the massive investment in AI setting us up for a painful correction in 2026? They dig into market concentration, inflated valuations, and why companies like Nvidia, Oracle, and OpenAI are raising red flags for some investors.
You’ll also hear why now is a smart time to rebalance your portfolio — but not the old way — and how high-net-worth investors are using buffered ETFs and direct indexing to level up their financial strategy. Plus, estate planning mistakes that can cost your heirs big time, and real answers in the Ask the Advisor segment — from embedded portfolio risk to downsizing dilemmas.
On this week’s Best of Simply Money podcast, Bob and Brian uncover the crucial differences between financial advisors who are just going through the motions and those truly playing offense—actively helping high-net-worth clients reduce taxes, build legacy plans, and take control of their financial futures. Learn the red flags that suggest your advisor may be stuck in the past and the proactive strategies—like Roth conversions and tax-efficient income planning—that can dramatically improve your long-term outcomes.
Plus, find out what Vanguard is doing that could make your 401(k) feel more like a pension, when it makes sense to start financially helping your kids now, and how to plan your estate beyond just taxes and probate. It’s a jam-packed show for anyone who wants to stay sharp and plan smarter.
On this episode of Simply Money presented by Allworth Financial, Bob and Brian reveal a stunning stat: just two companies—Alphabet and Nvidia—are responsible for a third of the S&P 500’s returns this year. If you think you’re diversified just because you own an index fund, think again. They dive into the historical precedent for today’s market concentration, the real risks of overexposure to big tech, and what smart investors should consider instead—including equal-weight ETFs, buffered products, and direct indexing.
On this week’s Best of Simply Money podcast, Bob and Brian break down the true art of asset location—why it’s not just about what you invest in, but where you hold those investments. They walk through real-life scenarios for high-net-worth investors, explaining how to use pre-tax, Roth, and taxable accounts to build smarter, tax-savvy portfolios. Then, Amazon, Alphabet, and Meta are flooding the market with corporate bonds. Why now? And what does that mean for income-focused investors? Plus, career expert Julie Bauke joins the show to unpack the “Executive Dilemma”—when to stay, when to jump, and how to evaluate your next big move. Also: tech-heavy indexes, the rise of private credit, and what to do with a lump sum after selling a rental property.
On this week’s Best of Simply Money podcast, Bob and Brian ask the question every long-term investor should be thinking about right now: while the headlines fixate on the Fed, are we focusing on the wrong thing? Plus, what a major move involving a media company can teach us about handling company stock. And don’t miss answers to your biggest financial questions, from capital gains strategy to whether ETFs really beat mutual funds in a taxable account.
On this week’s Best of Simply Money podcast, Bob and Brian explore how your financial plan should stay steady even when the economy doesn’t follow the script. From the double-digit interest rates of the 1980s to the AI-fueled market surge of 2023–24, they unpack the mixed signals investors have faced over the last 40 years—and what you can learn from the surprises. They also dive into how innovations from State Street could reshape your 401(k), how to make smart open enrollment choices, and real-life listener questions about supporting aging parents and adult kids, selling a business, managing inconsistent income, and dealing with old annuities.
On this week’s Best of Simply Money podcast, Bob and Brian dive deep into the AI investment craze that’s dominating headlines. Are we too late to cash in? Or is this just the beginning of a new economic era? They break down the hype, the risks, and the smarter way to invest—without trying to pick a winner. Plus, why international investing may deserve another look, a fresh update on the real estate market, and how to break out of financial decision paralysis. Finally, your listener questions on giving, planning, and the fear of running out—even when you have enough.
On this week’s Best of Simply Money podcast, Bob and Brian welcome former Cleveland Fed President Dr. Loretta Mester for a rare insider’s view into how interest rate decisions are made, why 2% inflation remains so elusive, and how the Fed stays focused amid political noise. She also recounts navigating the economy through COVID and shares what makes Ohio’s economy uniquely resilient.
Then, Bob and Brian shift gears to dissect huge earnings reports from Microsoft, Meta, Alphabet, and Nvidia — and what they signal for the future of AI and market momentum.
Later, they tackle real-life listener questions: why muni bonds might trigger “phantom income,” how mutual funds can lead to unexpected tax bills, tips for coordinating insurance policies, and whether investing through an LLC offers tax or liability advantages.
On this week’s Best of Simply Money podcast, Bob and Brian challenge the myth of the "magic number" in retirement planning. Just because you've hit $2 million or even $5 million doesn’t mean your future is locked in. Plus, hear stories of high-net-worth individuals navigating the pitfalls of poorly structured wealth. Later, they discuss new research showing that early retirement might actually shorten your life, how to use your empty nest phase for a financial makeover, and whether it’s possible to be too diversified. Finally, as always, Bob and Brian take on real listener questions—from restricted stock units to the right time to downsize.
On this week’s Best of Simply Money podcast, Bob and Brian celebrate the third birthday of the latest bull market — and reflect on what an 85% rise in the S&P 500 since 2022 really teaches long-term investors. Then, they explore a hidden risk for high-net-worth investors: complacency. When your wealth grows, it’s easy to think it’ll manage itself. Bob and Brian share how rebalancing, tax strategies, and proactive planning can keep success from turning into vulnerability. Plus, the team answers your most pressing financial questions about Roth IRAs, 5% CDs, and more.
On this week’s Best of Simply Money podcast, Bob and Brian warn against the “paper wealth trap” — mistaking market highs for lasting financial security. They break down how to turn temporary gains into durable wealth with proper liquidity, diversification, and planning. You’ll also hear why buffered ETFs are drawing billions from investors — and when they actually make sense. Plus, real estate pro Michelle Sloan joins to weigh in on the age-old question: rent or buy? And in ‘Ask the Advisor’ — smart moves for deferred comp plans, protecting company stock, and selling rental properties tax-smartly.
On this week’s Best of Simply Money podcast, Bob and Brian unpack the “smart-sounding” money advice that can quietly sabotage your future—from skipping Roth conversions and “going broke safely” in cash, to estate-planning myths that lead to probate messes, and being sold permanent life insurance instead of building a tax-smart strategy. Plus, they tackle oversized RMDs, executor pitfalls with business interests, smarter stock-option exercises, and whether to migrate from mutual funds to ETFs or direct indexing.
On this week’s Best of Simply Money podcast, Bob and Brian get Allworth Chief Investment Officer Andy Stout’s take on the Fed’s latest rate cut and what it really means for investors. They also cover new IRS rules pushing high earners’ 401(k) catch-ups into Roths, why HSAs are the most overlooked tax break, and how to protect your retirement from sequence of return risk. Plus, real listener questions on private REITs, pensions, and illiquid wealth—and a quick December tax trick that could save you thousands.
On this week’s episode of Simply Money, Bob and Brian put on their “tough teacher hats” to deliver some advice you may not want to hear, but absolutely need to hear. Just because you’ve saved $2 million, $3 million, or even $5 million doesn’t mean you’re automatically set for life. Their lessons cover why retirement isn’t a vacation but a paycheck replacement plan, why your kids don’t need another check but a financial strategy, how treating your portfolio like a casino can wreck decades of hard work, and why taxes could cost you more than your house. Plus, they dive into the real spending patterns of retirees, scams targeting families, and listener questions on concentrated tech stock, charitable remainder trusts, and how to plan for estate taxes on illiquid assets like real estate.
On this week’s episode of Simply Money, Bob and Brian break down the growing role of alternative investments inside retirement plans — and why you should be cautious before diving in. They also tackle whether today’s AI excitement is the new dot-com bubble, the lessons behind a shocking $4 million hospital bill, and what nearly 600,000 new 401(k) millionaires can teach us about long-term discipline. Plus, you’ll hear a personal story about how being overconcentrated in one stock devastated a family financially. And in our listener Q&A, we cover farmland sales, retirement income strategies, umbrella insurance, global diversification, and whether direct indexing beats ETFs.
On this week’s Best of Simply Money podcast, Bob and Brian break down what the Fed’s preferred inflation gauge is signaling and why mortgage rates may stay stubbornly high despite potential rate cuts.
They also explain new tax rules coming in 2026 that could change how you give to charity, and highlight a new study showing many retirees may outlive their savings.
Plus, they unpack the “action trap” that even smart investors fall into, compare retirement systems around the world, and tackle your questions on umbrella insurance, capital gains, risk tolerance in marriage, and managing tech-heavy portfolios.
Markets are up, Nvidia is booming, and Taylor and Travis are engaged — but what does any of that mean for your financial plan? On this week’s Best of Simply Money podcast, Bob and Brian cut through the noise to show why successful investors don’t chase fads or panic over headlines. From maximizing cash yields to making smart decisions about Roth conversions, inheritances, and even prenups, Bob and Brian explain how discipline and planning — not hype — are what protect and grow wealth.
Ever wonder why even the smartest financial plans sometimes fail in real life? On this week’s Best of Simply Money podcast, Bob and Brian unpack the four invisible forces—emotional, social, generational, and logical—that quietly drive every financial decision you make. From keeping up with friends at dinner parties to the money scripts you inherited from your parents, they’ll reveal how these hidden influences can sabotage your best-laid plans—and how to get back in control.
Bob and Brian also dive into common estate, investment, tax, and insurance mistakes high-net-worth families. Plus, what divorcing couples often overlook financially, and how to avoid being one of them.
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