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 haven” many expected in 2022, how to think strategically about 401(k) contributions across pre-tax, Roth, and after-tax buckets, and answer listener questions on retirement withdrawals, dividend income, and spending in early retirement.

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, 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.

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 protect both your lifestyle and your legacy.

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 families, and why proactive conversations around aging parents can prevent financial and emotional chaos later on.

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.

On this week’s Best of Simply Money podcast, Bob and Brian unpack the seven most common financial lies we tell ourselves – from “I’ll be happy when I have more money” to “I’ll figure it out on my own.” These aren’t just small white lies; they’re deeply emotional narratives that can quietly sabotage your financial future. Whether you're navigating lifestyle creep, market timing fears, or generational silence around money, this episode helps you recognize these self-deceptions and replace them with smart, actionable advice. Plus, tips for protecting your finances through divorce, estate planning updates you might have missed, and the growing threat of elder cyber scams.

On this week’s Best of Simply Money podcast, Bob and Brian unpack the booming world of alternative investments—from gold and crypto to private equity and real estate. Is now the time to diversify beyond stocks and bonds? Plus, what big bank earnings tell us about the economy, what a Cincinnati real estate expert sees in 2026, and how to financially support aging parents without derailing your own retirement. And if you waited until now to think about your 2025 taxes—don’t worry, there’s still time.

On this week’s Best of Simply Money podcast, Bob and Brian reveal why January is the most strategic money month of the year. From harvesting capital gains and revisiting direct indexing strategies to maximizing donor-advised funds and managing idle cash, they break down the smartest financial moves you can make right now. Plus, they discuss why a bigger tax refund isn't necessarily a good thing, how poor timing can erode your investment returns, and how to prepare emotionally and financially for long-term care decisions. Later, they answer listener questions about tax alpha, inherited IRAs, and consolidating retirement accounts.

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.