Laugh When The Market Crashes

Hosted by Terry Wheeler

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May 2026

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About the show

Welcome to “Laugh When The market Crashes” with Terry Wheeler, founder, and CEO of WE Alliance Wealth Advisors. In a world where choices abound, this podcast is your guide to help you unravel your unique complexities so you can enhance your financial portfolio and achieve personal fulfillment. Whether you’re a seasoned lawyer, a pioneering entrepreneur, a visionary CEO, or a distinguished medical professional, let Terry and his guests provide you with practical advice and actionable steps for a clearer perspective on the choices that matter most to you.

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34 recent

May 11, 202637 min

How to make Money with Short Term Rentals (Ep. 35)

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

May 1, 2026Episode 3432 min

Ai: Friend or Foe? (Ep. 34)

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.

April 22, 2026Episode 3324 min

Understanding Risk In Investing (Ep. 33)

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

February 13, 202623 min

Tax Concepts to Master in 2026 (Ep. 32)

On this episode of the WE Money Talk podcast, Terry Wheeler breaks down the fundamentals of powerful tax planning, and why most investors and high earners unknowingly leave significant money on the table each year. Rather than focusing only on investments, Terry introduces the core tax framework every successful tax strategy is built upon: understanding how income is taxed, how deductions actually work, and how different “tax buckets” interact. You’ll learn the critical differences between taxable, tax-deferred, and tax-free accounts, why timing matters more than most people realize, and how strategic planning can help reduce ordinary income — often the most heavily taxed form of earnings. Terry also walks through the three primary income buckets (ordinary income, capital gains, and passive income) plus the powerful fourth category where advanced strategies, especially real estate planning, can unlock meaningful deductions. Whether you’re a business owner, investor, or high-income professional, this episode lays the foundation for smarter tax decisions and explains why effective tax planning starts long before year-end. If you want to keep more of what you earn and understand how advanced strategies create six-figure deductions, this Tax Planning 101 episode is the place to start. In this episode, you’ll discover: How different investment accounts are taxed and why diversification across tax types matters The “tax bucket” framework advisors use to structure effective deduction planning How capital gains, passive losses, and real estate strategies interact under IRS rules Why waiting until October or November is often too late for meaningful tax savings The foundational concepts required before implementing advanced tax strategies Download the slides from this episode HERE. Connect with Terry Wheeler: WE Alliance Wealth Advisors 1-800-355-8174 terry@weriaadvisors.com LinkedIn: Terry Wheeler Facebook: WE Alliance Wealth Advisors, Inc YouTube: WE Alliance Wealth Advisors, Inc

December 23, 202521 min

2026 Predictions: : AI Agents, Humanoid Robots & The Future of Investing (Ep. 31)

Is 2026 the year robots finally enter our homes and AI takes over the office? In this episode of We Money Talk, we dive deep into the major trends arriving fast in 2026. From the explosion of humanoid robotics and “AI Agents” to the tokenization of real estate on the blockchain, the world is changing rapidly. We discuss how these technologies will revolutionize healthcare, impact the job market (Wall Street vs. Main Street), and what it all means for your investment portfolio. Are we heading for a market crash or an AI-fueled boom? Watch to find out where the “boring” investment opportunities lie in this high-tech future. In This Video, We Cover: The future is arriving fast Robotics in Manufacturing: Efficiency vs. Layoffs Humanoid Robots: $20k price points & home assistance. The “Terminator” Scenario: Safety, AI sympathy & kill switches . AI Agents: How co-pilots are changing the workforce. Blockchain Adoption: Real estate tokenization & liquidity Healthcare Revolution: Remote surgery, protein folding & longevity. Market Outlook: Is the stock market overextended? Where to Invest: Finding value in “boring” companies The future of skilled trades & conclusion.

December 8, 2025Episode 3020 min

My 15 Year Old Daughter, and Newly Published Author Zoey Wheeler: A Proud Dad Moment (Ep 30)

In this special 20-minute episode, WE Alliance Wealth Advisors founder Terry Wheeler sits down with his 15-year-old daughter, Zoey Wheeler, who recently became a published author. This heartfelt conversation offers a rare, behind-the-scenes look at Zoey’s writing journey and the moments that shaped her path to becoming a young novelist. Find Zoey’s new book Viewers will hear Zoey share: What first sparked her interest in writing How her debut novel came to life The challenges she navigated along the way How she balances school, creativity, and everyday life Her advice for other young writers with big dreams This episode is both an inspiring celebration of youthful creativity and a proud dad moment for Terry and the WE Alliance community. If you enjoy this conversation, be sure to like, comment, and subscribe for more episodes from WE Alliance Wealth Advisors. #ZoeyWheeler #TeenAuthor #FamilyPodcast #ProudDadMoment #WritingJourney #WEAlliance #WealthAdvisors #InspiringStories Connect with Terry Wheeler: http://weriaadvisors.com 1-800-355-8174 terry@weriaadvisors.com LinkedIn: Terry Wheeler: https://www.linkedin.com/in/terry-wheeler-jd-cfp/ Facebook: WE Alliance Wealth Advisors, Inc: https://www.facebook.com/WEAllianceWealthAdvisors Terry Wheeler is an Investment Adviser Representative of WE Alliance Wealth Advisors, Inc., a SEC-registered investment adviser located in Roseville, CA.

October 22, 2025Episode 2925 min

Learn From My Previous Investment Mistakes (Ep. 29)

In this incredibly candid episode titled “Learn From My Previous Investment Mistakes,” Terry Wheeler gets real about the financial blunders of his past the “scary investments” so you can secure your future without making the same costly errors. Terry covers three illiquid investment blunders and the one common mistake you need to address right now as the market nears its peak: Illiquid REITs & BDCs: Why did investments that were perfect in theory turn into decade-long traps with only modest (or negative) returns? The answer is fees and illiquidity. Learn why you must prioritize control. The Scaled Tax Lien Strategy: An example of a good idea ruined by flawed implementation. Terry explains the dangers of boutique investments that try to scale too fast. The Biggest Lesson: Market Defense! Relive the pain of the 2001 and 2008 crashes. Terry explains that his biggest mistake was not having a heavy enough concentration in protected positions near the market top. Actionable Takeaway: Terry advocates for Defined Outcome Investing to protect your gains and ensure you’re positioned to “buy the dip” when the current bull run inevitably ends. Find out how to achieve most of the upside with critical downside protection. Don’t wait to get crushed. Learn from these mistakes and take action today! Connect with Terry Wheeler: WE Alliance Wealth Advisors 1-800-355-8174 terry@weriaadvisors.com LinkedIn: Terry Wheeler Facebook: WE Alliance Wealth Advisors, Inc YouTube: WE Alliance Wealth Advisors, Inc

August 22, 2025Episode 2814 min

7 Lessons from the Titanic (Ep. 28)

On episode 28 of the WE Money Talk podcast, Terry Wheeler, a financial planner and estate attorney, takes a unique approach to financial planning by using the Titanic as a cautionary tale. He draws seven compelling lessons from the ship’s tragic story and applies them directly to your own financial journey. Discover how the same threads of overconfidence, ignored warnings, and a lack of preparedness that led to the demise of the “unsinkable” ship can also threaten your financial security. Terry breaks down the parallels, offering crucial insights on how to mitigate risks, create a robust plan, and ensure your financial future doesn’t hit an iceberg. Connect with Terry Wheeler: WE Alliance Wealth Advisors 1-800-355-8174 terry@weriaadvisors.com LinkedIn: Terry Wheeler Facebook: WE Alliance Wealth Advisors, Inc YouTube: WE Alliance Wealth Advisors, Inc

August 4, 2025Episode 2716 min

Trump’s New Tax Law: The Big Beautiful Bill (Ep. 27)

Navigate the 2025 tax season with confidence! This video breaks down the most impactful federal tax law changes for individuals and business owners under the new “One Big Beautiful Bill Act.” Discover how permanent lower tax brackets, a new senior deduction for Social Security, and a special deduction for tipped income could benefit you. Plus, business owners will learn about expanded QBI, boosted SALT deductions, and enhanced depreciation rules. Get practical tips to optimize your tax planning for 2025 and beyond! Connect with Terry Wheeler: WE Alliance Wealth Advisors 1-800-355-8174 terry@weriaadvisors.com LinkedIn: Terry Wheeler Facebook: WE Alliance Wealth Advisors, Inc YouTube: WE Alliance Wealth Advisors, Inc

June 5, 2025

Washington Update and Your Portfolio (Ep. 26)

What happens when common sense meets political reality? In this straight-shooting episode, Terry Wheeler tackles the uncomfortable truth about Washington’s fiscal dysfunction and why America’s long-term success depends on courage, not convenience. As economic pressures mount and global tensions rise, Americans are left wondering: Will our leaders step up—or just focus on re-election? Terry shares his unfiltered take on tariffs, taxes, and the toxic short-term mindset infecting both parties. With his signature clarity and conviction, he explains why real leadership requires more than rhetoric—and how the business community (and voters) can hold decision-makers accountable. This episode isn’t about left or right—it’s about what’s right for America’s future. Key discussions in this week’s release include: Why tariffs might actually be the best economic move for the U.S. right now The bipartisan elephant in the room: we need to both raise taxes and cut spending Why most politicians are smart, but selfish, and what that means for future generations A call for long-term thinking, straight from Terry’s own experience as a business leader and father And more! Resources: Maximizing Your Social Security Benefits (Ep. 20) Can I Depend on Social Security for My Retirement? (Ep. 8) Strategies for a Long, Healthy Retirement With Heather Holmes (Ep. 13) Understanding the Economic Impact of Trump’s Second Term (Ep. 18) What The Economy Could Look Like With Donald Trump As President (Ep. 16) Connect with Terry Wheeler: WE Alliance Wealth Advisors 1-800-355-8174 terry@weriaadvisors.com LinkedIn: Terry Wheeler Facebook: WE Alliance Wealth Advisors, Inc YouTube: WE Alliance Wealth Advisors, Inc