The holiday season inspires generosity, but smart gifting can go far beyond festive moments and gifts under the tree. On the show this week, we're digging into the world of gifting strategies, just in time for the end of 2025. Whether you're navigating last-minute holiday shopping, planning gifts for loved ones, or looking to maximize your charitable donations, this episode is packed with practical advice and fresh ideas.

We break down everything from tax implications of gifting cash, stocks, and even real estate, to making the most of donor-advised funds and qualified charitable distributions to help you balance generosity with smart financial planning, so you can give with both a warm heart and a wise mind.

• 00:00 Balancing gifting and planning.
• 03:18 Choosing between gifting or inheriting.
• 09:13 Tax implications of gifting stocks.
• 11:42 Caution when gifting non-cash assets.
• 15:17 Tax deductions and SALT limit.
• 17:29 2026 tax changes for donations.
• 20:46 Tax benefits of stock donations.
• 25:00 Qualified charitable distributions explained.
• 27:30 Tax-efficient inheritance strategies.

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📰 See the full show notes here

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We talk with hundreds of individuals and families every year, and many of the questions they ask come back to one core concern. Can my retirement plan really survive the messy, unpredictable situations that happen in real life. Instead of only looking at straight line projections or average returns, Chad and Allison walk through how to "stress test" your plan with real world what if scenarios so you can build confidence before a crisis hits.

In this episode, you will hear three of the biggest what if questions clients have been asking over the past year.

• What happens if there is a major market crash right as you retire?
• What if you retire earlier than expected, either by choice or by force?
• What if there is a major health shock for you or your spouse?

Rather than focusing on doom and gloom, the goal is to rehearse these situations on paper so that when life happens, you already have a plan for how to respond.

We also share a simple three-step framework you can use to run your own retirement stress test at home. You will learn how to identify the what-ifs that matter most to you, estimate their impact on your spending and timeline, and choose proactive moves that make your plan more resilient. Along the way, they discuss sequence of returns risk, health insurance bridges before Medicare, using taxable brokerage accounts strategically, and how to think about funding future healthcare needs without overpaying for insurance you may not need.

Outline of This Episode

• [00:00] Retirement stress testing.
• [04:50] Key questions to ask about a 25 to 50 percent portfolio decline, spending flexibility, and your safety bucket.
• [09:20] Transition to scenario two, early retirement before age 65 and why health insurance is such a critical factor.
• [13:30] Cash in the bank versus long term growth.
• [17:20] Healthcare shocks and long term care needs that can show up later in retirement.
• [21:00] How HSAs, disability insurance, and understanding your deductibles and out of pocket maximums fit into the picture.

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📰 See the full show notes here

🌐 Sign up here to receive a detailed pre-retirement checklist to ensure you are positioned to experience your ideal retirement.

When people think of what could haunt their retirement, they often imagine running out of money, facing unexpected expenses, or living too long. But as we discuss in this episode, there's a more insidious villain: sequence of return risk.

Sequence of return risk refers to the threat of poor investment returns occurring early in your retirement years, just when you start withdrawing funds. Even if the average returns over your retirement are sufficient, early losses can irreparably damage your nest egg and dramatically increase the odds of running out of money.

To bring these concepts to life (with a Halloween twist), we walk through a scenario featuring Jamie Lee Curtis's iconic character, Laurie Strode, imagining her retirement through 25 years of market ups and downs. The outcome all depends on her initial withdrawal strategy and, crucially, how her portfolio is allocated.

• [00:00] A Halloween retirement survival tale, ft. Laurie Strode.
• [03:16] Retirement withdrawal scenarios analysis.
• [07:30] Optimizing financial asset allocation.
• [11:47] Diversification protects retirement portfolios.
• [15:16] Retirement portfolio stress testing.
• [16:41] Retirement planning for stability.

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📰 See the full show notes here

🌐 Sign up here to receive a detailed pre-retirement checklist to ensure you are positioned to experience your ideal retirement.