Laugh When The Market Crashes

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...

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...

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...

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.

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...

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...

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 wher...

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...

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...

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 f...

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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Terry Wheeler is on a mission to provide young people with the financial education they often lack in school.  Growing up in a blue-collar family, he witnessed firsthand how hard work alone wasn’t enough to build wealth. His journey from struggling with debt after college to successfully leveraging investments to pay it off has shaped …

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What if your grasp of today’s political changes could truly affect your finances and future investments? Terry Wheeler delves into the pressing issues that President Donald Trump faces as he embarks on his second term. He tackles government debt, the reality behind employment numbers, and the challenges of achieving energy independence. Terry discusses:  The challenges …

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What trends will shape your financial decisions in 2025? Terry Wheeler reflects on the surprising twists of 2024 and anticipates the challenges and opportunities of the coming year. He touches on key movements in stocks, the unexpected rise of crypto, and the critical shifts in real estate and federal debt.  Terry discusses:  Market surprises and …

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What could a second term for Trump mean for the economy? In Episode 15, Terry shared his insights on the potential implications of a Kamala Harris presidency. Now, let’s explore what a Trump win could bring. Join Terry as he analyzes the impact of Trump’s policies on both Wall Street and Main Street, inflation trends, …

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When it comes to casting your ballot, it’s crucial to base your decision on facts, not emotions. Look for leaders who provide solid information and realistic solutions, not just empty promises. In this episode, Terry Wheeler breaks down Kamala Harris’ proposed economic policies, covering everything from government spending to taxation, and what they could mean …

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Reverse mortgages have evolved into a widely accepted financial tool, offering tailored solutions for certain individuals—particularly seniors seeking to enhance their financial security. Although there are costs involved, such as mortgage insurance, the potential relief and flexibility these products offer can make a meaningful difference in the lives of those in need. Join Terry Wheeler …

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On today’s episode of WE Money Talk, discover how custom life expectancy assessments like Halo can help you plan smarter for the future. Understanding your unique life expectancy can revolutionize your financial planning and ensure you don’t outlive your money. Join Terry Wheeler as he discusses the critical topic of longevity planning with Heather Holmes, …

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At age 73, you’re required to withdraw roughly 3.8% from your retirement account yearly. But did you know that proper planning can convert these withdrawals into tax-free money for your kids? In this installment we continue our How To Protect Your Loved Ones series by exploring strategic ways to make your IRA work harder for …

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How can you secure your family’s future beyond a simple will? Terry Wheeler delves into advanced estate planning, unveiling essential strategies to assist your loved ones before and after you have passed away. He navigates the complexities of California law, highlights the critical distinctions between wills and trusts, and offers an in-depth guide to crafting …

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Is your child looking to start a small business? How much do they understand about entrepreneurship and goal planning?

Join Terry Wheeler and his guest, VP of Digital Marketing at WE Alliance, and Executive Programs Director of WE Care, Jennifer Theuriet. Together they shed light on the crucial skills not currently taught in school that can propel students and young adults toward long-term success. 

From Terry’s journey of building businesses from a young age to the mission and goals of the WE Care Foundation, this episode is packed with inspirational stories, actionable advice, and the...

Conversations about the stock market can get chaotic quickly – especially because these past few years have tested even the most steadfast investors.  Has volatility and uncertainty become the new norm? How can you plan for a future that could change on a dime? Terry Wheeler dispenses pearls of wisdom with a steady hand, offering …

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Social Security was introduced in 1935 as a safety net for those few precious years post-retirement when life expectancy hovered around 61-65 years. In today’s era of extended lifespans, retirement stretches out into vast expanses of time, potentially spanning decades. Yet, amidst this horizon of possibility, the pressing questions that loom in many minds are: …

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Are you ready to uncover the truths and myths about long-term care and its implications for your financial future?  Terry Wheeler dives deep into the complexities and concerns surrounding long-term care (LTC). From dismantling common myths to exploring the real costs and solutions, Terry offers valuable insights and strategies to make informed decisions. Listen as …

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Are bonds your only fixed-income option?  In today’s episode of WE Money Talk, Terry Wheeler and his guest Matt Williams open the vault of fixed-income options going way beyond traditional bonds. From index crediting strategies to real estate lending and distressed debt opportunities, they discuss the importance of diversification and understanding risk tolerance in building …

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Inflation has the same effect as taxes, and the US government knows this. They play a game with inflation to effectively tax people, and they do it in a way that relates to the national deficit. Join host Terry Wheeler, CFP®, and Gabe Rodriguez, Investment Advisor at WE Alliance Wealth Advisors, Inc., as they delve …

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It’s not what you make, but what you keep that matters. That’s exactly what tax planning is about — keeping more of your hard-earned wealth! However, you need to be proactive about it. To learn how, listen to this informative podcast where Terry Wheeler, JD, CFP®, unravels the intricacies of tax planning. He shares a …

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How long will you live?  You might be lucky enough to reach your 90s, so what do you need to do now to make sure that your retirement savings last your lifetime? Join Terry Wheeler as he dives into the concerns of longevity, the importance of long-term planning, and how changing retirement income sources impact …

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What does your first meeting with WE Alliance Wealth Advisors look like? Listen in as Terry Wheeler walks you through the initial meeting experience and sheds light on the integral role it plays in shaping a successful financial journey. Gain insights into the revolutionary Retirement 360 Optimizer, an innovative tool designed to navigate the multifaceted …

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Welcome to We Money Talk with your host, Terry Wheeler, CEO at WE Alliance Wealth Advisors, Inc. For his inaugural episode, Terry tells stories of how at 15, he lied about his age so he could get a job and earn money, how he got his start as a stockbroker and financial advisor, and to …

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