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.

What do wealthy retirees do differently when it comes to spending, investing, and managing their financial future? In this episode of Protect Your Assets, David Hollander shares key lessons from decades of working with high-net-worth clients. You’ll hear insights on purposeful spending, systematic investing, team-based planning, debt strategies, and staying ahead of tax changes. Plus, David covers current market updates, crypto milestones, and signs of a cooling labor market.

Thinking about selling your business? In this episode of Protect Your Assets, David Hollander discusses key considerations for business owners preparing for a potential sale. From cleaning up your books to understanding valuation methods like EBITDA and discounted cash flow, you’ll learn how to navigate the transition thoughtfully.

David also explores tax implications, legal planning, and how to approach the emotional side of letting go of a company you’ve spent years building. Whether you’ve received a call from a private equity firm or you’re just beginning to consider your next chapter, this episode offers practical insights from over 30 years of working with business owners at every stage of the exit process.