Tag: Financial Advisor
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

Connect with Terry:
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
Investment & Retirement Blind Spots (Ep. 36)

Investment & Retirement Blind Spots (Ep. 36)

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Laugh When the Market Crashes | Uncovering Hidden Retirement Blind Spots with Terry Wheeler & Mike Saunders

Is your retirement portfolio truly prepared for a major market crash? In this episode of Laugh When the Market Crashes, Terry Wheeler sits down with Mike Saunders to unpack the critical difference between getting to retirement and getting through retirement.

Discover why traditional strategies like the standard 60/40 portfolio and relying solely on diversification might leave your savings vulnerable—and how a defined outcome investing approach can protect your downside so that “zero is your hero” when market downturns strike.

Key Takeaways From This Episode:

  • Getting To vs. Through Retirement: Why the portfolio strategy that grew your wealth shouldn’t be the same one you use for withdrawals.

  • The Danger of the 60/40 Portfolio: How withdrawal rates in a declining market can rapidly deplete long-term savings.

  • Defined Outcome Investing: Using private pensions, volatility buffers, target positions, and capped/buffered strategies to systematically buy the dip.

  • Fixing Hidden Tax Leaks: Why proper asset location between IRAs and non-qualified accounts matters just as much as returns.

Ready to identify the blind spots in your retirement plan?

Schedule a portfolio review and learn how our integrated planning approach can help bring true peace of mind to your financial future:

👉 Visit us at: https://www.weareiadvisors.com

Subscribe to the Channel: Don’t forget to hit the subscribe button and the notification bell so you never miss an episode of Laugh When the Market Crashes.

#RetirementPlanning #WealthManagement #MarketVolatility #FinancialAdvisor #DefinedOutcomeInvesting #LaughWhenTheMarketCrashes #PortfolioDefense #InvestingStrategy
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: 
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.