Tag: Retirement Planning
Retirement Income Blind Spots (Ep. 39)

Retirement Income Blind Spots (Ep. 39)

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Having a $2–3 million portfolio doesn’t guarantee a comfortable retirement. The real question is whether that lump sum can become reliable monthly income that lasts as long as you do.

In the fourth installment of the Blind Spot Series, Mike and Terry Wheeler look at the gap between what retirees have and what they’ll actually need. Terry explains why the strategies that built your nest egg can quietly drain it in retirement, and how to build a portfolio designed for cash flow, inflation, and longevity.

In this episode:

  • Securing a base level of income you can’t outlive, through Social Security, pensions, and private pensions
  • Why $15,000 a month today could mean $30,000 a month 15 years from now
  • Planning for the “go-go” and “slow-go” years of retirement
  • Why the classic 60/40 portfolio can put your income at risk
  • How defined outcome investing adds defense to your portfolio
  • Laddered bonds versus bond funds when interest rates rise
  • How proactive tax planning can close an income gap without adding risk
  • Longevity analysis and why your personal life expectancy should shape your Social Security, pension, and insurance decisions
  • The difference between a salesperson and a true financial advocate

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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
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.

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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!

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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:

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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.
Financial Strategies for a Long, Healthy Retirement With Heather Holmes (Ep. 13)

Financial Strategies for a Long, Healthy Retirement With Heather Holmes (Ep. 13)

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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 Lumiant. They delve into the significance of custom life expectancies and their impact on financial decisions. Heather opens up about her journey and the inspiration that led to the creation of Halo, a groundbreaking tool for personalized longevity assessments.

Key highlights include:

  • The role of custom life expectancy assessments in planning for your retirement
  • Halo’s personalized longevity reports and how they can help you make smarter financial decisions
  • The implications of life expectancy on social security and pension optimizations
  • How to plan for healthcare and long-term care costs accurately

Resources:

Connect with Terry Wheeler: 

Connect with Heather Holmes:

About Heather Holmes: 

Heather Holmes is the Founder and CEO of Genivity (acquired by Lumiant), an innovative WealthTech SaaS platform at the nexus of health and wealth for financial planning and wealth management strategies.