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Latest Episodes
Are You Really Ready to Retire? Take the 34-Point Checklist Challenge
August 4, 2025Considering 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 Big, Beautiful Bill: Tax Changes and Deadlines to Know
July 28, 2025The 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.
5 Retirement Blind Spots You Can’t Afford to Ignore
July 21, 2025What 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Your Assets, David Hollander explores five commonly missed areas that can impact your retirement experience; such as outdated estate planning, shifting tax laws, rising healthcare costs, underestimated longevity, and a potential loss of purpose post-retirement.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.
7 Common Retirement Mistakes—and Smarter Ways to Plan Around Them
July 14, 2025Turning 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.
Can You Afford to Retire? What to Know About Retirement Health Care Costs
July 7, 2025In 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.
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