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Why Appreciated Assets Might Be Your Best Gift Yet

Coffee with Your Retirement Coach

Release Date: 08/01/2025

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Coffee with Your Retirement Coach

In today's conversation, we tackle a reality more people are facing: living to 100 is becoming the new normal. Over the last century, we've been gifted an extra 30 years of life expectancy, but this blessing comes with serious questions. Will our health hold up? Will our money last? The old "retire and die in a few years" model is officially broken, and we need a completely different approach to planning. Together, Randy, Nic, and Aaron explore what it really takes to thrive through a 30-year retirement.   From the #1 "medication" for quality longevity (spoiler: it's not a pill) to the...

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Coffee with Your Retirement Coach

If you’re over 50 and even *thinking* about probate, accidental inheritance, or whether your estate plan will actually work the way you intend—it’s time to grab a cup of coffee and lean in. In today’s episode, we dive into the real-world estate planning mistakes we see far too often, and why having “the documents” doesn’t necessarily mean you have a plan. We unpack why so many well-intentioned families still end up in court, accidentally disinherit loved ones, or create unnecessary taxes and family tension. From wills vs. beneficiary forms to revocable living trusts, family...

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Coffee with Your Retirement Coach

In today’s conversation, we sit down with our friend and leadership giant Mark Cole, CEO of Maxwell Leadership Companies, for a powerful deep dive into what it truly looks like to move from success to significance—especially as we enter retirement or the pre-retirement years. This episode is packed with insights on purpose, identity, calling, and what it means for us to step into the next chapter of life with clarity and excitement rather than uncertainty.   Together, we explore the internal shifts that happen when we transition out of a title or high-pressure role, the mindset needed...

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Coffee with Your Retirement Coach

In this special Thanksgiving episode, we explore how cultivating an attitude of gratitude can be a game-changer for your mental wellbeing - even when you've achieved significant success in life. I share why some of the most accomplished people can actually feel miserable despite their achievements, and how a simple gratitude exercise can transform your perspective during challenging times. My colleagues and I discuss our favorite Thanksgiving traditions (I'm partial to deviled eggs while my co-host loves smoking turkey), but we quickly dive into the powerful psychology behind gratitude...

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Coffee with Your Retirement Coach

In this episode, Nic and I break down one of the most misunderstood concepts in estate planning: step-up in basis. We explain what basis is, why a step-up matters, and how common mistakes can cost your loved ones thousands in unnecessary taxes. If you've ever nodded along in conversations about basis while having no idea what it means, this episode is for you! We share real-world examples of how adding children to property deeds and accounts before death can create massive tax implications that could have been easily avoided with proper planning. TIMESTAMPS 00:00 - Introduction to basis and...

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Coffee with Your Retirement Coach

In this Halloween-themed episode, Nic and I dive into the three scariest assumptions that can haunt your retirement plans. Making the wrong assumptions about healthcare costs, taxes, and inflation can turn your golden years into a financial horror story! We break down shocking statistics about healthcare expenses in retirement (a healthy 65-year-old may need up to $320,000!), explain why your tax bill might actually be higher in retirement than during your working years, and discuss how inflation continues to erode purchasing power. Most importantly, we provide actionable strategies that may...

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Coffee with Your Retirement Coach

Let’s be honest — not everyone loves talking about money. In many marriages, one spouse takes the financial lead while the other says, *“It’s just not my thing.”* But what happens when the person who handles the finances isn’t around anymore?   In this episode of *Coffee with Your Retirement Coach*, I sit down with **Coach Nic Yeomans** to talk about how couples can protect themselves — and each other — financially. We break down how to plan, organize, and communicate around money, even when it feels uncomfortable or confusing.   Whether you’re the spouse who...

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Coffee with Your Retirement Coach

You asked, and we listened. In this episode of Coffee with Your Retirement Coach, we tackle one of the most common questions we get: "I’m 58 and have $2.4 million saved. Can I retire?" But as you'll hear, it’s not just about the number on the page. We dive deep into what that figure could mean for your income, lifestyle, taxes, healthcare, and overall retirement vision. Join us as we break down the math behind the 4% rule and explore the often-overlooked factors that make or break a retirement plan—things like purpose, timing, Social Security strategy, and where and how you want to live....

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Coffee with Your Retirement Coach

What would you do if your company sold, your stock was cashed out, and you suddenly found yourself with $5 million in hand? In this episode, Nic and I dive into the reality of experiencing a once-in-a-lifetime windfall and all the opportunities — and challenges — that come with it.   We explore the first critical steps you need to take before making big financial decisions, from understanding the tax implications to planning for long-term income and security. Whether you’re dreaming of retiring tomorrow or just trying to figure out what Uncle Sam’s cut will be, this conversation...

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Coffee with Your Retirement Coach

You’ve done it—you hit your retirement number. 🎉 Now what? In this episode, Nic and I walk through how to shift from saving to spending with intention: building a paycheck from your portfolio, deciding when (and how) to use Roth dollars, and coordinating taxes and healthcare so you don’t accidentally create avoidable costs. We also talk through a real-world success story and the four biggest takeaways I want you to leave with—without spoiling the details. If you’re wondering how to turn a lifetime of saving into a confident, sustainable retirement income plan, press play.  ...

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In this episode, we tackle one of the most overlooked and impactful ways to give—through appreciated assets. Whether you’re thinking about supporting your church or blessing a loved one, we break down how to give more wisely and tax-efficiently. This conversation was inspired by a listener from Marietta, and we couldn’t resist diving deeper into this topic that stirs up both generosity and smart planning.

Join Randy, Nic, and me (Aaron) as we explore two powerful angles: giving to charities versus giving to individuals. You’ll hear real-life stories, key strategies to avoid unnecessary taxes, and tips on how to be generous without creating financial complications for your recipients. If you’ve ever wondered whether to write a check or gift appreciated stock instead—this episode’s for you.

Episode Timeline:

  • [0:00] Welcome & Introduction
  • [0:30] Two Paths for Giving: Cash vs. Appreciated Assets
  • [1:08] Giving to Charity: The Charitable Version
  • [2:09] Real-Life Example: Gifting to Family
  • [4:16] Gift Tax Rules & Bracket Management
  • [5:38] Special Considerations: Disabilities & Financial Aid
  • [7:27] Generosity Spurs Generosity
  • [8:24] Key Takeaways & Final Thoughts
  • [8:54] Disclaimers & Contact Info

Key Takeaways:

  • Donating appreciated assets can help you avoid capital gains taxes and provide a bigger benefit to charities.
  • Gifting investments to family members in lower tax brackets can be a win-win, but be mindful of gift tax limits and special situations.
  • Always seek professional advice to ensure your generosity doesn’t unintentionally impact someone’s benefits or financial aid.

Links & Resources:

Thanks for being generous with your time. If you enjoyed today’s episode, please follow, rate, and share the podcast. And don’t forget to leave us a review—your feedback helps us serve more coachable people like you!

🛑 Disclaimer: Your Retirement Coach is a registered investment adviser. Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any specific securities, investments, or investment strategies. Investments involve risk and, unless otherwise stated, are not guaranteed. Be sure to first consult with a qualified financial adviser and/or tax professional before implementing any strategy discussed herein. Past performance is not indicative of future performance.