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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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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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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Tax planning often slips to the bottom of our financial to-do lists—until a surprise bill or missed opportunity crops up. But behind the scenes, the right process for an ongoing tax strategy can put you leagues ahead, reducing uncertainty and helping you capitalize on changes. On the show this week, we'll walk through the seven stages of tax planning, highlighting key insights and practical actions you can take.

• 00:00 Holistic Tax Planning Overview
• 01:56 Understanding clients' overall current situation and future goals
• [03:11] Importance of staying up-to-date for maximizing client opportunities
• [05:05] Importance of gathering detailed, current financial information:
• [06:50] Identifying tax planning opportunities and potential pitfalls by life stage
• [09:53] Adjusting withholding, making estimated payments, and managing expectations
• [13:19] Identifying and quantifying strategic tax planning actions
• [18:34] Examples of in-year tax planning

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Planning for retirement isn't just about hitting your savings targets and hoping for the best. It's about getting creative, asking new questions, and challenging your own assumptions.

We follow the retirement planning journey of a fictional couple, Dwight and Angela, who are three to five years from retirement, using the SIFT framework shared by Rohit Bhargava and Ben duPont in their book "Non-Obvious Thinking", to shed light on hidden financial opportunities.

• [00:00] Broadening perspectives on retirement strategies.
• [03:11] Making time to reflect to get better clarity on retirement plans.
• [07:05] Expand your perspective by looking for alternative experiences and advice beyond typical financial practices.
• [11:05] Focus on solving the right problem to combat overwhelming options.
• [14:58] Explore other investment opportunities like a business 401k, HSA, or brokerage account.
• [17:35] Coordinated financial planning strategies for our case study couple.

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Planning for your child's college education can feel overwhelming, especially when faced with skyrocketing tuition costs and countless savings options. This week on the show, we're discussing the question of exactly how much you should save in a 529 college savings plan.

• [00:00] Decide your college funding goal before saving in a 529 account.
• [02:06] An overview of college costs.
• {02:35] Advantages of the 529 Plan.
• [03:54] Weighing college savings vs. retirement savings.
• [05:31] What happens if I save too much?
• [07:35] Expanded legislation as part of the OBBB.

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Recently, an executive order has set the stage for 401 (k) providers to potentially start offering investments like private equity, private real estate, digital assets (think bitcoin), commodities, and more—options typically reserved for pension funds and institutional investors. But what does this really mean for everyday savers?

We break down the differences between traditional 401k offerings and these new alternatives, discuss the risks and potential rewards, and share questions you should ask yourself before making any changes to your investment lineup.

• [00:00] Exploring 401k alternative assets.
• [05:56] 401k market shift & fee impact.
• [06:57] Potential high returns vs. risks.
• [11:06] Private equity and closed-end funds.
• [13:59] The differences between public REITs and private real estate.
• [16:34] Private investments and evaluating portfolio fit.

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