Best of Simply Money

Riding Record Highs, AI Investing Myths, and the Senior Housing Crunch

On this week’s Best of Simply Money podcast, Bob and Brian dig into what investors should—and shouldn’t—do when the stock market keeps hitting record highs. Should you cash out or lean in? Behavioral finance, loss aversion, and portfolio strategy all come into play. Plus, hear how tools like direct indexing, buffered ETFs, and structured notes can help high-net-worth investors stay smart amid the noise.
Then, a reality check on retirement: new data reveals more Americans tapping their 401(k)s early, and a growing crisis in senior housing—especially right here in Cincinnati. Are you making a dangerous assumption about what Medicare actually covers? We’ll walk through the risks of waiting too long to secure care solutions.
Also in this episode: the truth about AI and investing—why even the smartest machine learning tools can't consistently beat the market, and how to actually use AI without falling for hype.

Your Mind vs. Your Money: How Emotions Quietly Derail Retirement

On this week’s Best of Simply Money podcast, Bob and Brian tackle the invisible force that can quietly wreck your retirement plan—your own mind. From action bias to overconfidence, scarcity to status quo traps, they unpack the psychological pitfalls that can sabotage even the best investment strategy.
Learn why your childhood money lessons still echo in your financial decisions today, how FOMO can lead to costly mistakes, and why behavioral coaching may be your greatest financial asset.
If you’ve built a solid nest egg but still feel anxious—or if you're tempted to chase trends like AI stocks—this conversation is a must-listen.

Financially Comfortable? The Hidden Risks You Can’t Afford to Ignore

Think you're financially secure? If you've got a solid portfolio, a vacation home, or even just a nice cushion saved up, this episode is for you. Bob and Brian uncover the overlooked threats that can sink your financial ship—from lacking umbrella insurance and cybersecurity exposure to the dangers of a sloppy estate plan.
They also tackle the pitfalls of over-concentration in company stock and the myth of diversification. Plus, how to fireproof your finances from family drama. If you’ve built wealth, now’s the time to protect it.

Midyear Market Check: Resilience Amid the Headlines

As 2025 hits the halfway mark, what do the markets, the economy, and your portfolio really look like? On this week’s Best of Simply Money podcast, Bob and Brian dissect the surprising strength of the markets despite geopolitical tensions, tariff fights, inflation fears, and political division. They explore what’s fueling the market’s growth, the role of earnings and inflation, and why long-term investors should stay the course.
Plus, insights into Kroger’s strategy shift, the truth about dividend reinvestment, key estate tax updates, and how life changes like retirement or divorce can—and should—reshape your financial plan.

Should You Bail on the Market During Global Chaos?

From wars and terror attacks to political strife, global events can shake our nerves—but should they shake our investments too? On this week’s Best of Simply Money podcast, Bob and Brian explore how markets have historically responded to geopolitical turmoil, and why staying the course with a solid financial plan could be your smartest move.
Plus, a deep dive into the boom in annuity sales and the real costs of those "guarantees," and an important warning about using AI for your online purchases.

The Life You Want, On Your Terms: Discover Financial Flexibility

Is the traditional idea of retirement outdated? On this week’s Best of Simply Money podcast, Bob and Brian challenge the old-school dream of "never working again" and introduce a more dynamic vision: financial flexibility. Discover how shifting your mindset—and your financial strategy—can unlock purpose, passion, and peace of mind in your later years.

Are You Rich or Just Comfortable? The Truth About Financial Independence

Think a $2 million nest egg makes you rich? On this week’s Best of Simply Money podcast, Bob and Brian break down the often misunderstood line between being wealthy and being truly financially independent. From benchmark net worth stats to the emotional rollercoaster that accompanies money management, they dive into the crucial questions every high-earner should ask themselves before and during retirement.
You’ll also learn why knowing your spending habits matters more than your net worth, how to build a guardrail strategy for market dips, the silent dangers of holding too much cash, and the emotional impact of delayed retirement. Plus, an estate planning expert joins the show to bust some common myths and share what most people overlook.
Whether you're nearing retirement or just curious about your financial future, this episode delivers practical advice with a dose of hard truth.

The #1 Mistake Even Smart Investors Make — And How to Fix It

On this week's Best of Simply podcast, Bob and Brian uncover the most common mistake even successful savers make with their money — and it’s not what you’d expect. Learn why having multiple accounts without a strategy could be sabotaging your financial future.
They also break down how to manage concentrated stock positions, the role of buffered ETFs in today's volatile markets, and why the first 10 years of retirement spending matter more than you think. Plus, a 5-minute task that could save you thousands in fraud protection. Don't miss these actionable insights to help secure your money now and for years to come!

Why Smart People Make Dumb Money Decisions

On this week’s Best of Simply Money podcast, Bob and Brian explore why even the smartest people can make lousy financial decisions — and what you can do to avoid the same traps.
Then, why Gen X may be facing the toughest retirement landscape yet… and what can still be done about it.
Plus, building your personal brand in retirement, and you ‘Ask the Advisor.’

The Value of Money, How to Stress-Test Your Portfolio, and Smart Options for High-Net-Worth Investors

On this week’s Best of Simply Money podcast, Bob and Steve take a step back from the usual market talk and get personal - asking a simple but powerful question: What does money really mean to you?
Is it security? Freedom? Maybe status? Everyone sees money differently, and Bob and Steve dig into how those views shape the financial decisions we make—often more with our hearts than our heads.
They also walk through how to stress-test your financial plan (without freaking out), and why emotions can sometimes throw logic out the window. Plus, hear how a solid plan can give you the freedom to live life on your terms—whether that’s retiring early, switching careers, or just sleeping better at night.
It’s a refreshingly real conversation about money, mindset, and making choices that actually fit your life.