Laugh When The Market Crashes

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 w...

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 &#...

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 leav...

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...

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 j...

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...

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 pe...

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 prep...

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...

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...

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 putting their retirement at risk...

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 adventure.  Discover the liberating world of budget travel...

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, Terry explores effective ways to show support and empa...

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 2001 and 2008, the episode...

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 you. Terry Wheeler discusses:...

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, like teachers and some government employees. Terry discusses...

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 his passion for teaching others. Through his program, Financial...

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 of managing government debt...

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 the importance of defense [00:00:41] The rising imp...

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, and the national deficit. This episode offers a thorough analysis a...

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 for the broader economy—a...

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 as he si...

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, CEO and founder of Genivity and Lum...

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 your heirs, covering essential strategies like RMD rescue plans, Ro...

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 a comprehensive estate plan tha...