For many car lovers, a classic or collector car represents memories, passion, and pride. Yet few owners stop to think about what happens to these valuable vehicles when they’re no longer around. In this episode of Protect Your Assets, David Hollander shares how estate planning can help protect both your car collection and your loved ones. He covers the importance of deciding whether heirs should keep or sell a vehicle, how placing cars in a trust can help avoid probate delays, and why appointing a special executor may make sense for unique assets like cars. You’ll also hear how to organize records and appraisals, what to know about capital gains rules and step-up in basis, and when charitable donations might provide tax advantages. Whether you own a single classic car or an entire collection, this episode offers practical guidance on preparing for the future while preserving what matters most.

Life insurance isn’t just for when you’re working—it can be a powerful tool in retirement. In this episode of Protect Your Assets, host David Hollander, The Sandman, breaks down whether retirees should keep their life insurance policies, how required minimum distributions (RMDs) can be converted into tax-free wealth for heirs, and why today’s interest rate environment may offer opportunities to upgrade existing coverage.

You’ll also learn:

• The key differences between term and permanent life insurance in retirement.
• How life insurance can supplement retirement income and provide long-term care benefits.
• Strategies for using life insurance to offset taxes, protect your spouse, or strengthen your estate plan.
• Tips for qualifying for coverage after age 65 and why underwriting rules matter.

Whether you’re approaching retirement or already there, this episode will help you evaluate your current policies, uncover hidden value, and decide if life insurance still belongs in your financial plan.

Are you confident your advisor is covering everything that matters for your retirement? In this episode of Protect Your Assets, David Hollander walks through a practical financial advisor checklist, including eight signs that reveal whether your advisor is truly providing comprehensive planning or just focusing on investments. From tax planning and Roth conversions to income strategies and team support, discover what could be missing from your plan and how to spot the red flags before it’s too late.

Thinking about a Roth IRA conversion in 2025? With tax rates locked in and new deductions available under the Big, Beautiful Bill, this year could be an ideal time to move funds from a traditional IRA or 401(k) into a tax-free Roth IRA. But timing is everything, and making the wrong move could increase your Medicare premiums or push you into a higher tax bracket. In this episode of Protect Your Assets, David Hollander explains how Roth conversions work, the benefits and risks in today’s tax environment, and strategies to determine the right amount to convert.

Considering retirement in the near future or already there? In this episode, David Hollander shares highlights from Liberty Group’s 34-point Retirement Checklist Challenge. The list covers questions about income planning, inflation, Social Security, real estate, and more, designed to help you think through the complexities of retirement. This episode offers a chance to evaluate where you stand and what steps may be worth considering next.

The 2017 tax cuts are no longer temporary. The Big, Beautiful Bill has locked in some provisions while introducing new rules, revised deductions, and expiration dates that affect income, charitable giving, estate planning, and retirement strategies.

In this episode of Protect Your Assets, David Hollander discusses:

Changes to tax brackets, deductions, and exemptions beginning in 2025 and beyond

How new rules may affect charitable contributions, gifting, and capital gain planning

Key considerations for trusts, Roth conversions, and required minimum distributions

Recent developments in stablecoins and crypto legislation

This episode highlights timelines and considerations to discuss with your financial, legal, or tax professional as you review your own plan.

What are the retirement blind spots many people fail to consider? In this episode of Protect Your Assets, David Hollander explores five commonly missed areas that can impact your retirement experience; such as outdated estate planning, shifting tax laws, rising healthcare costs, underestimated longevity, and a potential loss of purpose post-retirement. He also discusses how the new “Big, Beautiful Bill” may affect existing trust structures. Understanding these blind spots can offer useful perspective as you evaluate your retirement plans.

Turning 65 soon? You’re not alone in worrying about outliving your savings. In this episode of Protect Your Assets, David Hollander, The Sandman, breaks down the seven most common mistakes that can quietly derail your retirement plans. From imbalanced portfolios to income stream gaps, healthcare costs, and spending patterns, we explore how small missteps can snowball over time. Whether you’re approaching retirement or helping a loved one prepare, this episode offers clarity around the risks and choices that matter most.

In this Fourth of July weekend episode of Protect Your Assets, David Hollander considers what financial freedom means in retirement, and the often-overlooked role of retirement health care costs. From navigating Medicare and long-term care options to assessing how health-related expenses may impact your retirement strategy, this episode offers a range of considerations to keep in mind. David also shares thoughts on recent economic developments, market trends, and the potential effects of the new Big, Beautiful Bill. Whether you’re approaching retirement or simply preparing for the future, this conversation is designed to help you think critically about what lies ahead.

Teaching kids about money is one of the most valuable gifts you can give them, and summer is the perfect time to start. In this episode of Protect Your Assets, David Hollander breaks down six essential lessons to help your children or grandchildren build healthy financial habits early.

You’ll learn how to:

Talk about earning, saving, and spending in relatable terms

Set up their first bank account or Roth IRA

Encourage entrepreneurship through simple side hustles

Turn everyday moments into teachable financial insights

Help them avoid common mistakes with practical, age-appropriate tools

If you’re a parent or grandparent looking for an easy way to start teaching kids about money, this episode is packed with actionable advice.