Portfolio Strategy & Risk

Learn how to evaluate portfolio returns, diversification, volatility, risk, and opportunity cost. These resources help investors look beyond averages and coordinate investments with liquidity, cash flow, protection, and long-term objectives.

The Best Cash-Flowing Assets and How to Build a Portfolio That Pays You

By Rachel Marshall / June 29, 2026 /

The default wealth-building playbook goes like this: buy something low, hope it’s worth more someday, then sell to capture the gain. That’s the appreciation model, and it can work. But it’s not the only path, and for a lot of business owners and high-income professionals, it’s not the most reliable one either. The Money Advantage…

Will AI Replace Financial Advisors? Why Wisdom Still Wins in Real Life Money Decisions

By Rachel Marshall / January 26, 2026 / Comments Off on Will AI Replace Financial Advisors? Why Wisdom Still Wins in Real Life Money Decisions

The Moment “Confident” Sounds Like “Certain” A few weeks ago, we found ourselves talking about how quickly AI is moving. It’s not just that it can answer questions fast—it’s that it can sound certain while doing it. And when you’re staring at a big money decision—debt, investing, taxes, retirement—certainty feels like relief. It feels like…

Financial Planning Mistakes: The Most Risky Moves Aren’t What You Think

By Rachel Marshall / January 12, 2026 / Comments Off on Financial Planning Mistakes: The Most Risky Moves Aren’t What You Think

Bruce said something on the show that stuck with me because it’s so honest: Everyone thinks they’re an aggressive investor… until they lose money. And it’s true. Most people don’t even realize the biggest financial planning mistakes they’re making until the moment something “unexpected” happens: a market drop, a job change, a medical curveball, an…

Questions a Good Financial Advisor Should Ask (But Most Don’t)

By Rachel Marshall / July 21, 2025 / Comments Off on Questions a Good Financial Advisor Should Ask (But Most Don’t)

I’ll never forget Bruce’s story about his car, the check engine light on, and a mechanic insisting it needed a $1,500 catalytic converter. Bruce knew better and fixed it by simply tightening the gas cap. That story isn’t just about auto repair; it perfectly illustrates why questions a good financial advisor should ask matter. Without…

The Truth About Investing Diversification: Why It’s More Than Just Spreading Risk

By Rachel Marshall / November 4, 2024 / Comments Off on The Truth About Investing Diversification: Why It’s More Than Just Spreading Risk

Have you ever been told not to put all your eggs in one basket? If you’ve been in the financial world for any amount of time, whether through your 401(k) or investing in the stock market, you’ve likely heard this advice. Investing diversification has long been hailed as a tried-and-true strategy for mitigating risk, ensuring…

How to Invest Like a Billionaire, with Richard Wilson

By Rachel Marshall / August 22, 2022 / Comments Off on How to Invest Like a Billionaire, with Richard Wilson

Want to get billionaire investing strategies and learn how to model the successful few? If you want to know how to invest like a billionaire, you’ll want to pay attention to our guest Richard Wilson. Today, we’re talking with Richard Wilson, CEO and Founder of the Family Office Club. Richard has helped create and formalize 100+…

5 Reasons Your Financial Plan is Failing

By Rachel Marshall / July 12, 2021 / Comments Off on 5 Reasons Your Financial Plan is Failing

Are you on track for financial freedom? If you don’t know the answer to this question, you’re not alone.  Most people think the answer is how much more they have left before the house is paid off, how much left on the student loans, the balance of their retirement fund, the stock market’s performance, the Federal…

Creating a Balanced Wealth Portfolio

By Rachel Marshall / June 28, 2021 / Comments Off on Creating a Balanced Wealth Portfolio

We like to ask our audience, what is your biggest challenge with building wealth, and we receive so many insightful questions. Today, we’re answering a question from Matt about how to create a balanced wealth portfolio.  So if you want to make sure you’re thinking through all the pieces of your financial plan and doing…

Are We at the Top of the Market?  How to NOT Lose Money

By Rachel Marshall / November 18, 2019 / Comments Off on Are We at the Top of the Market?  How to NOT Lose Money

After seeing an upward trend in the markets over the past decade, you may be concerned that we’re at the top of the market cycle.  Many people are feeling the volatility and uncertainty.  How do economic factors direct your decision-making?  Should you stay in for the long haul and ride it out? In today’s show,…

What to Do With Tax-Deferred Investments for Business Owners

By Rachel Marshall / October 21, 2019 / Comments Off on What to Do With Tax-Deferred Investments for Business Owners

Tax deferral may seem like the epitome of smart financial planning.  But tax-deferred investments can be a tricky trap like the spiderwebs that caught Frodo in Lord of the Rings. How should you think about retirement accounts if you’re a business owner? In today’s conversation, we answer: What is tax deferral? What are the underlying…

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