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Taxes & Tax Blind Spots (Ep. 37)

Taxes & Tax Blind Spots (Ep. 37)

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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 can potentially save six to seven figures over your lifetime.

In This Episode, We Cover:

  • Reactive Filing vs. Proactive Planning: Why your CPA is too busy during tax season to build long-term wealth strategies—and why planning belongs in the fall.

  • The “Two Sets of Tax Codes”: How knowing advanced tax strategies transforms a financial planner from a portfolio expense into a high-return profit center.

  • Beyond the Standard Roth Conversion: Advanced methods, including discounted Roth conversion strategies and tax stacking to aggressively lower or eliminate conversion taxes.

  • Multi-Generational & Large IRA Strategies: Navigating Required Minimum Distributions (RMDs), the 10-year inherited IRA rule, and using charitable tax approaches to protect family wealth across generations.

  • The High-Income Payout Trap: Strategic moves (such as residency planning and structured deferrals) to legally mitigate massive state and federal tax bills on large lump sums.

Keep More of What You’ve Built Taxes are often the single largest fee you will pay in retirement. Don’t let Uncle Sam be an equal partner in your nest egg. Learn how our fully integrated financial and tax planning approach helps you retain wealth and step into retirement with confidence.

👉 Connect with our team: https://www.weareiadvisors.com

Don’t Forget to Subscribe: So you never miss an episode of Laugh When the Market Crashes.

#TaxPlanning #RetirementPlanning #WealthManagement #RothConversion #InheritedIRA #FinancialAdvisor #LaughWhenTheMarketCrashes #ProactiveTaxPlanning #TaxStrategy
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.
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: 
Washington Update and Your Portfolio (Ep. 26)

Washington Update and Your Portfolio (Ep. 26)

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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 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: 
How to Travel the World Before You Retire with Ed Wheeler (Ep. 24)

How to Travel the World Before You Retire with Ed Wheeler (Ep. 24)

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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 adventure. 

Discover the liberating world of budget travel and learn about Ed’s adventures across Tbilisi, Malta, and Prague. His experiences will inspire you to plan your own life-enhancing journeys, encouraging you to see the world and embrace flexibility without waiting for the “right time.”

Key conversation points include:

  • The life changes that pushed him towards early travel [00:02:41] 
  • Why Tbilisi, Georgia, became his destination of choice [00:04:38] 
  • Insights from Malta’s medieval charms to Prague’s bustling neighborhoods [00:18:12]
  • How to blend work and travel in the Cayman Islands [00:32:58] 
  • And more!

 

Resources:

Connect with Terry Wheeler: 

 

Connect with Ed Wheeler:

  • (303) 972-2443

About Ed Wheeler: 

Ed Wheeler is an Executive Consultant with Long International and has over 35 years in the heavy civil construction, oil and gas, and power industries. He is experienced with the development of pre-bid pursuit schedules and baseline schedules and recently completed a pursuit schedule for a $1.3 billion joint venture project.

Mr. Wheeler has had a significant role in the development of large, sophisticated project schedules for several high-profile nationwide projects totaling over US$8 billion. He has proven experience in construction management, management advisory services, and construction claims consulting. He provides clients with superior hands-on industry knowledge and the analytical and problem-solving skills necessary to understand and demonstrate the effects of complex construction issues and time-related impacts.

Mr. Wheeler began his career as an Operating Engineer for one of the largest U.S. heavy civil contractors. He subsequently worked as a Project Engineer, Project Manager, Project Scheduler, Contract Administrator, Scheduling Consultant, Senior Scheduler, and Corporate Scheduler. Mr. Wheeler has provided services to several of the most respected heavy civil contractors in the U.S. and some of the largest construction companies in the world.
Maximizing Your Social Security Benefits (Ep. 20)

Maximizing Your Social Security Benefits (Ep. 20)

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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, like teachers and some government employees.

Terry discusses:

  • The history and misconceptions around Social Security. [00:00:41]
  • Major changes for 2025 and their implications for cost-of-living adjustments. [00:02:59]
  • Adjustments on retirement age and contributions. [00:05:03]
  • The Social Security Fairness Act and who it affects. [00:09:06]
  • How you could recoup benefits retroactively and what steps to take next. [00:12:22]

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.
Understanding the Economic Impact of Trump’s Second Term (Ep.18)

Understanding the Economic Impact of Trump’s Second Term (Ep.18)

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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 of managing government debt [00:00:38]
  • Understanding real employment numbers vs. headline figures [00:03:45]
  • The role of tariffs and national security [00:06:34]
  • Energy independence and its economic impact [00:11:13]
  • Strategies for tackling immigration thoughtfully [00:16:37]
  • The potential effects of reducing government size and regulation [00:26:17]
  • 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.
What The Economy Could Look Like With Donald Trump As President (Ep.16)

What The Economy Could Look Like With Donald Trump As President (Ep.16)

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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, and the national deficit. This episode offers a thorough analysis and actionable advice to help you navigate the evolving economic landscape. 

Episode discussions include:

  • Learn about the potential market impacts of Trump’s spending strategies
  • Understand how tariffs and regulations might affect inflation and business growth
  • Explore Trump’s stance on energy independence and foreign policy implications
  • Consider how potential immigration reforms could influence Main Street and Wall Street.

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.

 
What The Economy Could Look Like With Kamala Harris As President (Ep.15)

What The Economy Could Look Like With Kamala Harris As President (Ep.15)

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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 for the broader economy—and your portfolio. Explore the nuances of a Harris presidency and how it might compare to a potential Trump economy, providing insights to help you prepare for what’s ahead.

Key episode discussion points include:

  • The historical significance of Harris potentially being the first female president and what this means for American symbolism
  • Harris’ possible spending policies, inclinations toward maintaining social programs, and implications for stock markets and inflation
  • Proposals for corporate tax rates and potential policy impacts on wealth distribution
  • Her position on energy independence and the administration’s effectiveness in border security and immigration policies

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.