Your portfolio just dropped 30%. Should you panic-sell, or is there a smarter move hiding in plain sight?

Financial planner Sean Mulaney joins Brad and Jonathan to break down five critical money moves during a market downturn. The conversation centers on staying calm during volatility and implementing tax-smart strategies that turn losses into long-term advantages.

Introduction and Overview [00:00:00]

The Importance of Staying Calm [00:01:53]

Understanding Tax Loss Harvesting [00:06:06]

Wash Sale Rules Explained [00:14:07]

Roth IRA Insights [00:33:24]

Strategizing Roth Conversions [00:44:43]

Conclusion and Call to Action [00:52:30]

Key Terms:

Related Episode:

▶ Listen Next: Ep. 206 — What Happens When Your Paycheck Stops: Retirement Planning Part 1 | Essential Listening

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When groceries cost $2 per person per meal, the impossible starts to sound doable. Brad and Laura Barrett spent years curating their "Top 50" recipe collection — not boxed mac and cheese, but actual gourmet-quality home cooking that keeps costs low without sacrificing flavor. After months of teasing, they've finally released it as a free downloadable cookbook.

This mashup episode covers multiple listener topics: the economics of smart meal planning, creative Mother's Day gift ideas including personalized celebrity messages from Cameo.com, and the launch of the Rebel Entrepreneur podcast with guest Alan Donegan. The conversation also touches on how the pandemic is reshaping education and what it means to prepare for success in an uncertain job market.

[00:01:00] Introduction to Meal Planning

[00:02:39] Economics of Meal Cooking

[00:10:00] Mother's Day Gift Ideas

[00:14:10] Rebel Entrepreneur Podcast Launch

[00:19:00] Financial Independence Discussion

[00:35:00] Education and the Future Job Market

How can I improve my grocery budget?

What is the Rebel Entrepreneur podcast about?

What are effective Mother's Day gifts?

How has COVID affected education?

What are the benefits of home cooking?

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Small landlords are collecting 90% of rent during a crisis — defying national headlines predicting widespread defaults. Chad Carson breaks down why relationships, not just numbers, separate resilient real estate portfolios from those at risk.

Chad Carson shares critical strategies for real estate investors navigating economic uncertainty. The conversation covers maintaining strong tenant relationships, calculating your burn rate, keeping adequate cash reserves, and identifying investment opportunities when markets shift. Carson reveals surprisingly high rent collection rates among small-scale landlords compared to alarming national statistics, and explains why proactive communication with tenants matters more than ever.

Tenant Management Strategies [00:07:11]

Liquidity and Cash Reserves [00:10:12]

Evaluating Investment Opportunities [00:23:34]

Cash Reserves [00:10:12]

Burn Rate [00:11:02]

1% Rule [00:26:22]

▶ Listen Next: Ep. 205 — Tax Loss Harvesting and Other Money Moves to Make During a Financial Crisis | Essential Listening

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You might assume the CARES Act's student loan payment pause is just a temporary break — but if you're on an income-driven repayment plan, those suspended months still count toward forgiveness. Travis from Student Loan Planner reveals how borrowers can reclaim thousands by understanding this quirk, and whether your debt-to-income ratio means you should chase forgiveness or pay off loans aggressively.

The core decision for student loan borrowers: repay in full or pursue forgiveness? Travis explains how federal loan repayment and forgiveness programs work under the CARES Act, which pauses both payments and interest. Critically, payments made (or not made) between March 13 and September 30 count toward income-driven repayment and forgiveness — even zero-dollar payments. Borrowers who made automatic payments during the pause can request refunds from their loan servicers.

[00:01:20] Overview of Student Loan Situations

[00:02:00] CARES Act and Student Loan Payments

[00:06:31] Understanding Loan Types and Forgiveness

[00:09:18] Strategies for Recent Graduates

[00:15:06] Key Insights on Loan Repayment and Interest

[00:24:21] Consultation and Resources

▶ Listen Next: Ep. 203 — Real Estate Investing During a Recession Or Financial Crisis With Coach Carson | Essential Listening

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Most people assume their 401k is locked until 59½, but the Rule of 55 allows penalty-free withdrawals nearly five years earlier—and hardly anyone knows it exists.

Brad and Jonathan break down this IRS provision, which lets you tap retirement funds if you leave your job during or after the year you turn 55. The catch? It only applies to your current employer's 401k or 403b, not old accounts. They explain who qualifies, what the restrictions are, and how this lesser-known rule can reshape your early retirement timeline.

The episode also features Jillian from Everyday Courage, who talks about moving forward when finances (or life) feel hopeless. Her message: progress doesn't require perfection, and small steps matter more than flawless execution. Brad and Jonathan round out the discussion with listener stories of debt payoff wins and creative anniversary celebrations during isolation.

[00:08:41] The Rule of 55: Accessing Your 401k Early

[00:28:37] Overcoming Hopelessness with Jillian from Everyday Courage

[00:01:09] Community Stories and Creative Connection

▶ Listen Next: Ep. 202 — Student Loan Planner with Travis Hornsby | Essential Listening

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Most investors can recite the phrase "buy and hold" in their sleep, but how many actually understand what they're holding? Stocks represent partial ownership in businesses—yet price swings, P/E ratios, and market sentiment can feel more like alchemy than arithmetic.

Brian Feroldi, a Motley Fool contributor, breaks down what actually makes a stock valuable. The core insight: stock prices rise because companies generate profits, not because of daily market drama or ticker symbols flashing green. He explains why the price-to-earnings ratio matters more than the share price itself, and why two $50 stocks can represent wildly different values depending on the earnings underneath.

The episode also tackles why markets react more to expectations than to actual news—good earnings can send a stock tumbling if investors anticipated better. Feroldi emphasizes that long-term profit growth is what drives business value, which is why index funds work: they capture the aggregate rise in corporate profits over time without requiring you to pick individual winners.

Introduction to Stocks [00:00:41]

Understanding Individual Stocks [00:01:50]

What Drives Stock Prices? [00:05:15]

The Role of P/E Ratio [00:11:01]

Market Sentiment vs. Actual Value [00:24:47]

Conclusion and Key Takeaways [00:40:18]

What is a stock?

How do stocks gain value?

What does the P/E ratio indicate?

How can market sentiment affect stock prices?

Why are index funds recommended?

Stock

P/E Ratio

Market Sentiment

Index Funds

▶ Listen Next: Ep. 201 — Rule of 55: Early Retirement Withdrawal Strategy | Essential Listening

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Withdrawing from your retirement portfolio during a market crash could derail decades of careful planning—but the solution isn't always to stop spending. Karsten from Early Retirement Now returns to tackle the single biggest threat to early retirees: sequence of return risk in unprecedented market conditions.

With COVID-era market drops unlike anything in modern history, the usual safe withdrawal playbook may no longer apply. Karsten dissects what this volatility means for people at every stage of financial independence—whether you're just starting out, halfway to your FI number, or already living off your portfolio. Counterintuitively, current valuations might mean some retirees can actually increase their withdrawal rates, while others face catastrophic portfolio damage if they continue business as usual.

Introduction to Retirement Discussions [00:00:00]

Market Behavior and Historical Context [00:09:15]

Strategies for Withdrawal Rates [00:14:00]

Portfolio Asset Allocation and Tax Implications [00:38:55]

Conclusion and Key Takeaways [00:45:55]

Sequence of Return Risk [00:05:29]

Safe Withdrawal Rate [00:17:02]

▶ Listen Next: Ep. 200 — Stock Market Fundamentals and Index Fund Investing | Essential Listening

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You can negotiate almost everything — but what about your relationship with risk during a market crash?

Brad and Jonathan tackle a packed mailbag covering mortgage payoff strategies, refinancing in a volatile market, and creative ways to cut costs like pausing car insurance. Listener Allie shares what budgeting actually looked like on the ground in China during strict pandemic lockdowns, offering practical negotiation tactics and proof that living well doesn't require high spending. The episode also unpacks how to think about optimism and calculated planning when the future feels uncertain — inspired by a previous guest's bullish take on market timing.

[00:01:20] Discussion on Optimism with Earn

[00:12:00] Listener Mailbag Questions

[00:14:49] Best approach to mortgage payments during uncertain times

[00:21:00] Related Resource: Refinancing Tips

[00:22:04] How to save money on car insurance

[00:33:00] Allie's Quarantine Insights

[00:40:54] Key Quote: "What story are you writing?"

[00:41:00] Jared's Success Story

"If Earn is optimistic, maybe it's time for me to view things similarly." [00:02:49]

"Remember, you can negotiate everything." [00:35:39]

"Living well doesn't require high spending." [00:39:30]

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You've already switched to grocery delivery, haven't you? Or maybe you're still white-knuckling it through crowded aisles, wrestling over the last can of beans. Jonathan Mendonsa and Brad Barrett compare notes on how lockdown grocery runs forced them to rethink shopping habits entirely — and discovered that delivery services like Instacart and Walmart pickup didn't just save time, they accidentally fixed their budgets by eliminating impulse buys. Beyond the grocery cart, they explore whether pandemic-era remote work flexibility is worth fighting for long-term, and close with a quick win: how to check if the government owes you money through unclaimed property databases.

Key Topics Discussed:

Adapting to Grocery Delivery

Embracing Remote Work

Unclaimed Property Tip

Key Quotes:

Chapter Markers:

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Millions unemployed, countless businesses shuttered, yet the stock market surged back from its lows. With experts Big ERN analyzing this disconnect through the lens of V-shaped, U-shaped, and L-shaped recovery scenarios, the conversation reveals why tracking weekly unemployment claims matters more than headlines and how dollar-cost averaging protects investors when certainty evaporates.

Key Topics:

Market vs. Economic Reality

Recession Characteristics

The 'Death Zone' Concept

Market Timing Challenges

Investment Strategy During Volatility

Key Insights:

Related Resources:

Timestamps:

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We work hard to keep ChooseFI ad-free for a clean listening experience. The easiest way to support us is to use our Top Recommended Cards page when signing up for your next travel rewards credit card.