Laugh When The Market Crashes

Laugh When The Market Crashes

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.

Episodes

October 16, 2026 • 18 mins

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 eg...

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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 Wheele...

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September 16, 2026 • 23 mins

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 ...

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    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 Cra...

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    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) S...

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    May 1, 2026 • 32 mins

    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 Read more

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    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,

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    February 13, 2026 • 23 mins

    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...

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    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 Str...

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    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 inter...

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    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 …

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    August 22, 2025 • 14 mins
    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 …

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    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, …

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    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 …

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    What if you could send your kids to college without sacrificing your financial future?  Many families find themselves caught in the middle of this challenge, but with the right approach, it’s entirely possible to balance both. Terry Wheeler provides practical insights into how families can make smarter financial decisions when planning for college expenses, without …

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    Feeling restless and considering an early escape from the daily grind? What if you could start living your dream retirement now, even before clocking out for good? Join Terry Wheeler as he chats with his brother, Ed Wheeler, about the concept of “mini retirements” and how this lifestyle can redefine your approach to wealth and …

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    What do we say when words seem inadequate?  In this heartfelt episode, Terry Wheeler delves into the complexities of grief and the challenges we face in supporting those who have lost a loved one.  Drawing from personal experiences and a compelling presentation he attended by Darren Sugiyama, a fellow financial advisor deeply affected by loss, …

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    Is your investment portfolio prepared for the storm ahead? With market warning signs on the horizon, discover how to turn potential downturns into opportunities for long-term growth. Terry Wheeler decodes the warning signals investors might be missing and shares insights on building a recession-ready portfolio. With guests exploring the history of past market crashes in …

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    Could refinancing your annuity turbocharge its return by 50% while also topping up your retirement fund with bonuses you don’t have to pay back?  Terry Wheeler dives into annuity refinancing strategies that are hard to ignore given today’s interest rate climate. If you’re curious about how your financial future could benefit, this conversation is for …

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    What does the Social Security Fairness Act mean for your retirement plans?  In this episode of WE Money Talk, Terry Wheeler unpacks the upcoming changes to the Social Security system that could impact your benefits. The Social Security Fairness Act is set to expand eligibility, proving vital for many who previously fell through the gaps, …

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