Category: Financial Services
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
Tax Concepts to Master in 2026 (Ep. 32)

Tax Concepts to Master in 2026 (Ep. 32)

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On this episode of the WE Money Talk podcast, Terry Wheeler breaks down the fundamentals of powerful tax planning, and why most investors and high earners unknowingly leave significant money on the table each year. Rather than focusing only on investments, Terry introduces the core tax framework every successful tax strategy is built upon: understanding how income is taxed, how deductions actually work, and how different “tax buckets” interact.

You’ll learn the critical differences between taxable, tax-deferred, and tax-free accounts, why timing matters more than most people realize, and how strategic planning can help reduce ordinary income — often the most heavily taxed form of earnings. Terry also walks through the three primary income buckets (ordinary income, capital gains, and passive income) plus the powerful fourth category where advanced strategies, especially real estate planning, can unlock meaningful deductions.

Whether you’re a business owner, investor, or high-income professional, this episode lays the foundation for smarter tax decisions and explains why effective tax planning starts long before year-end. If you want to keep more of what you earn and understand how advanced strategies create six-figure deductions, this Tax Planning 101 episode is the place to start.

In this episode, you’ll discover:

  • How different investment accounts are taxed and why diversification across tax types matters
  • The “tax bucket” framework advisors use to structure effective deduction planning
  • How capital gains, passive losses, and real estate strategies interact under IRS rules
  • Why waiting until October or November is often too late for meaningful tax savings
  • The foundational concepts required before implementing advanced tax strategies

Download the slides from this episode HERE.

Connect with Terry Wheeler: 
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.
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!

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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:

Connect with Terry Wheeler: 
Money for College: Conventional and Unconventional Sources (Ep. 25)

Money for College: Conventional and Unconventional Sources (Ep. 25)

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What if you could send your kids to college without sacrificing your financial future? 

Many families find themselves caught in the middle of this challenge, but with the right approach, it’s entirely possible to balance both.

Terry Wheeler provides practical insights into how families can make smarter financial decisions when planning for college expenses, without putting their retirement at risk. 

The conversation focuses on strategies that can help families save more effectively and avoid common pitfalls that lead to financial stress down the road.

Key discussion points include:

  • Navigating conventional and unconventional sources of college money [00:07:17]
  • Decoding the real costs involved in higher education [00:05:26]
  • Innovative tax credit and deduction strategies to save on college expenses [00:20:21]
  • The power of income shifting and 529 plan tactics [00:33:11]
  • Business-savvy methods to maximize tuition funding [00:31:14]
  • And more!

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.
What to Say (and Not Say) to Someone Grieving (Ep. 23)

What to Say (and Not Say) to Someone Grieving (Ep. 23)

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What do we say when words seem inadequate? 

In this heartfelt episode, Terry Wheeler delves into the complexities of grief and the challenges we face in supporting those who have lost a loved one. 

Drawing from personal experiences and a compelling presentation he attended by Darren Sugiyama, a fellow financial advisor deeply affected by loss, Terry explores effective ways to show support and empathy.

Terry shares touching stories about his late friend, Bruce Bone, and reflects on how to meaningfully connect with grieving families. 

Gain insight into navigating grief as this episode covers:

  • Grief Etiquette: What to say and, just as importantly, what not to say to those in mourning.
  • Personal Stories: Recounting memories and finding comfort in shared experiences. 
  • Acts of Kindness: The impact of unexpected gestures and memorials that honor lost loved ones. 
  • Practical Support: Offering tangible help without adding pressure during difficult times.

Connect with Terry Wheeler: