Tag: We Alliance Wealth Advisors
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
Learn From My Previous Investment Mistakes (Ep. 29)

Learn From My Previous Investment Mistakes (Ep. 29)

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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)

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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: 
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: 
Unlocking Annuity Potential & How Refinancing Could Boost Your Returns (Ep. 21)

Unlocking Annuity Potential & How Refinancing Could Boost Your Returns (Ep. 21)

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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 you.

Terry Wheeler discusses:

  • What refinancing an annuity involves and its potential benefits [00:00:49]
  • The economic environment making annuity upgrades viable [00:02:25]
  • Different types of annuities and eligibility for refinancing beginning at [00:03:29]
  • Financial implications, including cap rates and par rates [00:06:29]
  • The tax implications of refinancing through a 1035 exchange [00:13:32]
  • And so much 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.
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.
Empowering the Next Generation with Financial Literacy (Ep.19)

Empowering the Next Generation with Financial Literacy (Ep.19)

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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 his passion for teaching others.

Through his program, Financial Foundations, Terry aims to teach financial fundamentals to a wide audience, from young teens to adults who never learned these essential skills. In this episode, he highlights how the program covers topics like saving early, compound interest, and investing. 

Highlights include:

  • The importance of financial education for young people [00:01:00]
  • Basics of saving, investing, and understanding debt [00:03:40]
  • Plans to bring financial lessons to schools and families [00:06:02]
  • Foundational concepts and advanced applications in wealth building [00:08:19]
  • 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.