Laugh When The Market Crashes

Hosted by Terry Wheeler

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Oct 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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38 recent

October 16, 2026Episode 3918 min

Retirement Income Blind Spots (Ep. 39)

Having a $2–3 million portfolio doesn’t guarantee a comfortable retirement. The real question is whether that lump sum can become reliable monthly income that lasts as long as you do. In the fourth installment of the Blind Spot Series, Mike and Terry Wheeler look at the gap between what retirees have and what they’ll actually need . Terry explains why the strategies that built your nest egg can quietly drain it in retirement, and how to build a portfolio designed for cash flow, inflation, and longevity. In this episode: Securing a base level of income you can’t outlive, through Social Security, pensions, and private pensions Why $15,000 a month today could mean $30,000 a month 15 years from now Planning for the “go-go” and “slow-go” years of retirement Why the classic 60/40 portfolio can put your income at risk How defined outcome investing adds defense to your portfolio Laddered bonds versus bond funds when interest rates rise How proactive tax planning can close an income gap without adding risk Longevity analysis and why your personal life expectancy should shape your Social Security, pension, and insurance decisions The difference between a salesperson and a true financial advocate Connect with Terry: Law firm: www.strategicwealthlegal.com Financial firm: www.weriadvisors.com Get the book: www.laughwhenthemarketcrashes.com

October 1, 2026Episode 3824 min

Estate Planning Blind Spots (Ep. 38)

Estate Planning Blind Spots: Why Most Living Trusts Fail (And How to Protect Your Family) Think having a revocable living trust means your estate plan is complete? For most families, standard "fill-in-the-blank" legal documents leave massive blind spots that can accidentally disinherit children, trigger unnecessary taxes, or leave wealth exposed to lawsuits and divorce. In this episode of Laugh When the Market Crashes, Terry Wheeler breaks down family-centered estate planning and why true legacy protection goes far beyond simply avoiding California probate. Discover how proactive legal and financial coordination keeps your wealth protected across generations. 🔗 Schedule a consultation & explore our retirement resources: 👉 https://www.weriaadvisors.com What You’ll Discover in This Episode: The "Check-the-Box" Trap: Why most basic revocable living trusts leave major gaps. Remarriage & Bloodline Protection: How surviving spouses unintentionally disinherit biological children and grandchildren. Invisible Divorce & Creditor Protection: Shielding your heirs’ inheritances from lawsuits, creditors, and ex-spouses. "Yellow School Bus" Liability: Safeguarding surviving spouses from catastrophic liability and freak accidents. Family-Centered Inheritance Planning: Using family banks and milestone-based distributions so wealth empowers the next generation rather than being spent in under three years. The 3-Step Estate Planning System: How regular updates and counseling-oriented guidance drastically reduce administration costs down the road. Key Moments & Timestamps: 00:00 – Introduction: What is More Important Than Legacy? 01:00 – Portfolio Defense & Tax-Efficient Estate Integration 02:58 – Why Avoiding Probate in California is Only Step One 06:17 – The Real Risks of "Fill-in-the-Blank" Living Trusts 07:23 – Remarriage & Bloodline Protection 10:43 – Guardianship Planning: Passing on Values, Not Just Money 12:28 – Divorce & Creditor Protection for Inheritances 13:30 – The "Yellow School Bus" Asset Protection Scenario 16:03 – Protecting Adult Heirs From Themselves: Family Banks & Gifting 17:42 – The 3-Step Ongoing Estate Planning Framework 19:56 – Real Case Study: Fixing a Blended Family’s Seven-Figure Estate Plan 23:42 – How to Connect with Terry Wheeler

September 16, 2026Episode 3723 min

Taxes & Tax Blind Spots (Ep. 37)

Laugh When the Market Crashes | The Retirement Tax Blind Spot with Terry Wheeler & Mike Saunders It’s not just about what you make it’s about what you keep . In this episode of Laugh When the Market Crashes , host Terry Wheeler joins Mike Saunders to break down the massive tax blind spots that catch high-earning professionals and retirees off guard . Discover why traditional tax preparation (reactively filling in forms during tax season) fails retirees, why a basic Roth conversion is only scratching the surface of tax strategy, and how a proactive, multi-generational tax plan can potentially save six to seven figures over your lifetime . In This Episode, We Cover: Reactive Filing vs. Proactive Planning: Why your CPA is too busy during tax season to build long-term wealth strategies—and why planning belongs in the fall . The “Two Sets of Tax Codes”: How knowing advanced tax strategies transforms a financial planner from a portfolio expense into a high-return profit center . Beyond the Standard Roth Conversion: Advanced methods, including discounted Roth conversion strategies and tax stacking to aggressively lower or eliminate conversion taxes . Multi-Generational & Large IRA Strategies: Navigating Required Minimum Distributions (RMDs), the 10-year inherited IRA rule, and using charitable tax approaches to protect family wealth across generations . The High-Income Payout Trap: Strategic moves (such as residency planning and structured deferrals) to legally mitigate massive state and federal tax bills on large lump sums . Keep More of What You’ve Built Taxes are often the single largest fee you will pay in retirement . Don’t let Uncle Sam be an equal partner in your nest egg . Learn how our fully integrated financial and tax planning approach helps you retain wealth and step into retirement with confidence . Connect with our team: https://www.weareiadvisors.com Don’t Forget to Subscribe: So you never miss an episode of Laugh When the Market Crashes . #TaxPlanning #RetirementPlanning #WealthManagement #RothConversion #InheritedIRA #FinancialAdvisor #LaughWhenTheMarketCrashes #ProactiveTaxPlanning #TaxStrategy

September 2, 2026Episode 3623 min

Investment & Retirement Blind Spots (Ep. 36)

Laugh When the Market Crashes | Uncovering Hidden Retirement Blind Spots with Terry Wheeler & Mike Saunders Is your retirement portfolio truly prepared for a major market crash? In this episode of Laugh When the Market Crashes , Terry Wheeler sits down with Mike Saunders to unpack the critical difference between getting to retirement and getting through retirement . Discover why traditional strategies like the standard 60/40 portfolio and relying solely on diversification might leave your savings vulnerable—and how a defined outcome investing approach can protect your downside so that “zero is your hero” when market downturns strike. Key Takeaways From This Episode: Getting To vs. Through Retirement: Why the portfolio strategy that grew your wealth shouldn’t be the same one you use for withdrawals. The Danger of the 60/40 Portfolio: How withdrawal rates in a declining market can rapidly deplete long-term savings. Defined Outcome Investing: Using private pensions, volatility buffers, target positions, and capped/buffered strategies to systematically buy the dip. Fixing Hidden Tax Leaks: Why proper asset location between IRAs and non-qualified accounts matters just as much as returns. Ready to identify the blind spots in your retirement plan? Schedule a portfolio review and learn how our integrated planning approach can help bring true peace of mind to your financial future: Visit us at: https://www.weareiadvisors.com Subscribe to the Channel: Don’t forget to hit the subscribe button and the notification bell so you never miss an episode of Laugh When the Market Crashes . #RetirementPlanning #WealthManagement #MarketVolatility #FinancialAdvisor #DefinedOutcomeInvesting #LaughWhenTheMarketCrashes #PortfolioDefense #InvestingStrategy

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.

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