Laugh When the Market Crashes Podcast Episode 35

How to Turn Short-Term Rentals Into a Massive Tax Shield (Zero Tax Roth Strategy)

Are you tired of losing a massive chunk of your income to taxes? In this episode of Laugh When the Market Crashes, host Terry Wheeler is joined by real estate expert Olivia Barrett to reveal one of the most powerful “tax stacking” secrets in the financial world: The Short-Term Rental (STR) Strategy. We dive deep into how a single Airbnb or VRBO property can generate a six-figure tax write-off against your ordinary income in year one. Whether you are a high-earning physician or a business owner, these rules could change your entire financial trajectory.

In this episode, we cover: The 100-Hour Rule: How to qualify for these deductions without being a full-time real estate pro. Cost Segregation Analysis: The math behind getting a $200k+ write-off in Year 1. The Zero Tax Roth Conversion: How to use your rental depreciation to move your retirement funds into a Roth IRA—totally tax-free. Market Spotlights: Why Nevada City, Kings Beach (Tahoe), and the UC Davis Med Center area are the current “hot spots” for STR investors. The Exit Strategy: What “Swap Till You Drop” means and how to use 1031 exchanges to build a legacy.

Connect with Terry Wheeler at

www.weriaadvisors.com

AI in Finance: Is Your Portfolio Being Managed by a Hallucination?

Artificial Intelligence is rewriting the rules of business, tax, and estate planning. But is it a revolutionary tool for wealth creation, or a “foe” that provides dangerous, incomplete data?

In this episode of Laugh When the Market Crashes, Terry Wheeler, J.D., CFP®, explores the dual nature of AI. From the risks of “legal hallucinations” in the courtroom to the powerful “tax overlays” that can add 1–3% to your annual returns, Terry explains why AI should be your collaborator, but never your pilot.

In this episode, we cover:

• The “Average Answer” Trap: Why basic AI often gives you the median of the internet’s “noise” rather than expert strategy.

• Risk Premiums & Portfolios: How we use AI to ensure your portfolio isn’t just a “Vanguard clone” but is capturing all five key risk premiums.

• The Attorney’s Cautionary Tale: Why relying on AI-generated research without human verification can be career-ending.

• Privacy & Security: The #1 rule for protecting your personal financial data when using LLMs.

• The Macro Picture: How AI and robotics will impact the middle class and the future of the 5-day work week.

Visit weriaadvisors.com to connect with Terry.

Welcome to the inaugural episode of the Laugh When the Market Crashes podcast (formerly WE Money Talk)!

In this episode, host Terry Wheeler, J.D., CFP®, dives deep into the primary risks that can derail your financial future. As Terry prepares to release his upcoming book, Laugh When the Market Crashes, he pulls back the curtain on why traditional “buy and hold” strategies often leave retirees vulnerable.

Whether you’re in the “sprint to retirement” or already enjoying your golden years, understanding these 10 risks is the difference between panic during a downturn and having the “quiet smile” of a prepared investor. Grab your coffee, roll up your sleeves, and let’s get to work.

In this episode, you’ll learn:

• Why Behavioral Risk (and FOMO) is your portfolio’s biggest enemy.

• The math behind Sequencing of Return Risk and why it’s “dumb luck” you can actually control.

• How Defined Outcome Investing provides a “defense” that can potentially increase your safe withdrawal rate.

• The massive “tax drag” that could be costing you half of your retirement wealth.

Connect with Terry at weriaadvisors.com