Tag: Certified Financial Planner
How to make Money with Short Term Rentals (Ep. 35)

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

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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) 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)

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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)

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

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

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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 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.
7 Lessons from the Titanic (Ep. 28)

7 Lessons from the Titanic (Ep. 28)

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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)

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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, 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: 
Are Reverse Mortgages Right for Your Retirement? (Ep. 14)

Are Reverse Mortgages Right for Your Retirement? (Ep. 14)

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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 as he sits down with Brooke McManus, Account Executive at Longbridge Financial, to unpack the modern-day reverse mortgage. Together, they dive into the key benefits, including how reverse mortgages can help address financial challenges, the common misconceptions that persist, and the critical costs to consider.

Key takeaways from this episode include: 

  • Associated costs and eligibility parameters of reverse mortgages 
  • Line of Credit (LOC) options and how they can benefit borrowers
  • Expert insights into the application process
  • How can reverse mortgages help fund in-home care, long-term care, or emergencies
  • And more

Connect with Terry Wheeler: 

Connect with Brooke McManus:

About Our Guest: 

Brooke McManus serves as an Account Executive for Longbridge Financial. With nearly a decade of mortgage and real estate industry experience, her client-centric approach to evaluating customer needs yields continually satisfied customers and strong, lasting partnerships. Brooke takes special pride in her ability to work with brokers of all experience levels, from industry veterans to those who are new to reverse mortgages.

 

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

 The information presented is for educational purposes only. No listener should assume that any discussions or information presented serves as the receipt of, or a substitute for, personalized advice from WE Alliance Wealth Advisors, Inc. or from any other investment professional and is not intended as an offer of solicitation for the sale or purchase of any specific securities, investments, or investment strategies. WE Alliance Wealth Advisors, Inc. is not a law firm or accounting firm, and no portion of this Podcast should be interpreted as legal, accounting, or tax advice. Information expressed does not take into account your specific situation or objectives and is not appropriate for every individual. Listeners are encouraged to seek advice from a qualified tax, legal, or investment adviser to determine whether any information presented may be suitable for their specific situation.

FEATURE
How To Protect Your Loved Ones: Estate Planning Essentials (Ep. 11)

How To Protect Your Loved Ones: Estate Planning Essentials (Ep. 11)

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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 a comprehensive estate plan that stands the test of time.

Terry touches on: 

  • Differences between revocable and irrevocable trusts
  • The importance of avoiding probate and understanding the probate process
  • Detailed strategies for protecting your estate from taxes
  • Unique protections like bloodline and remarriage protections
  • And more

Connect with Terry Wheeler: 

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

 The information presented is for educational purposes only. No listener should assume that any discussions or information presented serves as the receipt of, or a substitute for, personalized advice from WE Alliance Wealth Advisors, Inc. or from any other investment professional and is not intended as an offer of solicitation for the sale or purchase of any specific securities, investments, or investment strategies. WE Alliance Wealth Advisors, Inc. is not a law firm or accounting firm, and no portion of this Podcast should be interpreted as legal, accounting, or tax advice. Information expressed does not take into account your specific situation or objectives and is not appropriate for every individual. Listeners are encouraged to seek advice from a qualified tax, legal, or investment adviser to determine whether any information presented may be suitable for their specific situation.

FEATURE
Can I Depend on Social Security for My Retirement? (Ep. 8)

Can I Depend on Social Security for My Retirement? (Ep. 8)

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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: ‘Will my financial resources endure?’ and ‘Can I truly rely on Social Security to safeguard my future?'”

Join Terry Wheeler, CFP® and host of WE Money Talk, as he tackles Social Security concerns head-on. Explore its future stability, benefit-maximizing strategies, and practical tips for retirement planning. From its origins to navigating demographic shifts, Terry provides straightforward advice for optimizing your Social Security benefits.

Key highlights include: 

  • The evolution of Social Security and its impact on retirement planning
  • How demographic trends influence Social Security’s financial health
  • Techniques to optimize your benefits based on life expectancy and financial resources
  • The role of alternative income streams, including private pensions
  • And more

Resources:

Connect with Terry Wheeler: 

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

 The information presented is for educational purposes only. No listener should assume that any discussions or information presented serves as the receipt of, or a substitute for, personalized advice from WE Alliance Wealth Advisors, Inc. or from any other investment professional and is not intended as an offer of solicitation for the sale or purchase of any specific securities, investments, or investment strategies. WE Alliance Wealth Advisors, Inc. is not a law firm or accounting firm, and no portion of this Podcast should be interpreted as legal, accounting, or tax advice. Information expressed does not take into account your specific situation or objectives and is not appropriate for every individual. Listeners are encouraged to seek advice from a qualified tax, legal, or investment adviser to determine whether any information presented may be suitable for their specific situation.