Laugh When The Market Crashes

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:

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:

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

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

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#TaxPlanning #RetirementPlanning #WealthManagement #RothConversion #InheritedIRA #FinancialAdvisor #LaughWhenTheMarketCrashes #ProactiveTaxPlanning #TaxStrategy

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

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#RetirementPlanning #WealthManagement #MarketVolatility #FinancialAdvisor #DefinedOutcomeInvesting #LaughWhenTheMarketCrashes #PortfolioDefense #InvestingStrategy

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

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:

Download the slides from this episode HERE.

Connect with Terry Wheeler: 

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.

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:

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

http://weriaadvisors.com

Terry Wheeler is an Investment Adviser Representative of WE Alliance Wealth Advisors, Inc., a SEC-registered investment adviser located in Roseville, CA.

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: