Category: Financial Management
How to make Money with Short Term Rentals (Ep. 35)

How to make Money with Short Term Rentals (Ep. 35)

By |

Podcast: Play in new window | Download | Embed

Subscribe: RSS | More

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: Friend or Foe? (Ep. 34)

Ai: Friend or Foe? (Ep. 34)

By |

Podcast: Play in new window | Download | Embed

Subscribe: RSS | More

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.
Understanding Risk In Investing (Ep. 33)

Understanding Risk In Investing (Ep. 33)

By |

Podcast: Play in new window | Download | Embed

Subscribe: RSS | More

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
Tax Concepts to Master in 2026 (Ep. 32)

Tax Concepts to Master in 2026 (Ep. 32)

By |

Podcast: Play in new window | Download | Embed

Subscribe: RSS | More

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: 
2026 Predictions: : AI Agents, Humanoid Robots & The Future of Investing (Ep. 31)

2026 Predictions: : AI Agents, Humanoid Robots & The Future of Investing (Ep. 31)

By |

Podcast: Play in new window | Download | Embed

Subscribe: RSS | More

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.
Learn From My Previous Investment Mistakes (Ep. 29)

Learn From My Previous Investment Mistakes (Ep. 29)

By |

Podcast: Play in new window | Download | Embed

Subscribe: RSS | More

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: 
7 Lessons from the Titanic (Ep. 28)

7 Lessons from the Titanic (Ep. 28)

By |

Podcast: Play in new window | Download | Embed

Subscribe: RSS | More

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 financial future doesn’t hit an iceberg.

Connect with Terry Wheeler: 
Trump’s New Tax Law: The Big Beautiful Bill (Ep. 27)

Trump’s New Tax Law: The Big Beautiful Bill (Ep. 27)

By |

Podcast: Play in new window | Download | Embed

Subscribe: RSS | More

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 QBI, boosted SALT deductions, and enhanced depreciation rules. Get practical tips to optimize your tax planning for 2025 and beyond!

Connect with Terry Wheeler: 
Washington Update and Your Portfolio (Ep. 26)

Washington Update and Your Portfolio (Ep. 26)

By |

Podcast: Play in new window | Download | Embed

Subscribe: RSS | More

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 his unfiltered take on tariffs, taxes, and the toxic short-term mindset infecting both parties. 

With his signature clarity and conviction, he explains why real leadership requires more than rhetoric—and how the business community (and voters) can hold decision-makers accountable.

This episode isn’t about left or right—it’s about what’s right for America’s future.

Key discussions in this week’s release include:

  • Why tariffs might actually be the best economic move for the U.S. right now
  • The bipartisan elephant in the room: we need to both raise taxes and cut spending
  • Why most politicians are smart, but selfish, and what that means for future generations
  • A call for long-term thinking, straight from Terry’s own experience as a business leader and father
  • And more!

Resources:

Connect with Terry Wheeler: 
Money for College: Conventional and Unconventional Sources (Ep. 25)

Money for College: Conventional and Unconventional Sources (Ep. 25)

By |

Podcast: Play in new window | Download | Embed

Subscribe: RSS | More

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. 

The conversation focuses on strategies that can help families save more effectively and avoid common pitfalls that lead to financial stress down the road.

Key discussion points include:

  • Navigating conventional and unconventional sources of college money [00:07:17]
  • Decoding the real costs involved in higher education [00:05:26]
  • Innovative tax credit and deduction strategies to save on college expenses [00:20:21]
  • The power of income shifting and 529 plan tactics [00:33:11]
  • Business-savvy methods to maximize tuition funding [00:31:14]
  • And more!

Connect with Terry Wheeler: