The first 100 days of retirement can feel a lot like bringing home a newborn—exciting, uncertain, and full of surprises. In this episode of Protect Your Assets, David Hollander explains why so many new retirees struggle during this transition and what you can do to prepare. From the loss of routine to changing relationships and financial adjustments, learn how to approach your first 100 days of retirement with clarity and confidence by focusing on five key pillars: income, investments, estate, health, and purpose.

When your health fails, families often bear the emotional and financial cost. In this episode of Protect Your Assets, David Hollander dives into long-term care planning, from real-life caregiving challenges to understanding the true cost of in-home and facility care. Learn how to evaluate caregivers, what long-term care can cost in California, and how veterans or their spouses may qualify for the VA’s Aid and Attendance benefit to help pay for care.

David also breaks down key RMD strategies for retirees age 73 and older, including how a QLAC can reduce taxable income and delay distributions. Plus, a brief market update and what to watch for as year-end approaches.

Is pet insurance worth the cost? In this episode of Protect Your Assets, David Hollander breaks down what pet insurance covers, how accident vs. accident-and-illness plans differ, and what to know about deductibles, reimbursement rates, and annual limits. He also highlights exclusions like dental cleanings, how premiums can vary by age and zip code, and options for puppies, kittens, or older pets with pre-existing conditions.

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.