The Scholar Wealth Podcast - Episodes Tagged with “Inheritance Planning”

Episode 51: Rachel Cruze of The Ramsey Show on Raising Money-Smart Kids, DAFs vs. Private Foundations, and Getting Into Alternatives

Scholar Financial Advising, LLC — Mon, 06 Apr 2026 05:00:00 -0400

This week, Rachel Cruze — author, speaker, and co-host of The Ramsey Show — joins Stephan for a candid conversation about the third-generation wealth trap, the mistakes well-intentioned parents make, and how to raise kids who can actually handle money. Rachel shares what it was like growing up as Dave Ramsey's daughter, how she's navigating those same questions with her own three kids today, and the one conversation she thinks every parent of means should be having right now.

We also answer two listener questions: a family giving $200,000 a year through a donor-advised fund wants to know whether a private foundation makes more sense — especially with four adult children who all want to be involved. And with equity markets showing real volatility, a listener in their mid-40s asks whether rental real estate is a smart way into alternatives, or whether they'd just be trading one set of risks for another.

Stay in touch beyond the podcast:

Newsletter: https://scholarfinancialadvising.com/newsletter

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Disclaimer: The information provided in this podcast is for general informational and educational purposes only, and is not intended to constitute financial, investment, or other professional advice. The opinions expressed are those of the hosts and guests and do not necessarily reflect the views of any affiliated organizations. Investing in financial markets involves risk, including the potential loss of principal. Past performance is not indicative of future results. Before making any investment decisions, you should consult with a qualified financial advisor who can assess your individual financial situation, objectives, and risk tolerance. Thanks for listening!

Episode 48: Stock Compensation, Inherited IRA Taxes, and Documenting Family Legacy

Scholar Financial Advising, LLC — Mon, 16 Mar 2026 05:00:00 -0400

Why do companies sometimes pay employees with stock instead of cash? And what happens when you inherit a multi-million-dollar IRA under the 10-year rule?

In this episode of the Scholar Wealth Podcast, we answer two listener questions that highlight how compensation structures and tax rules shape financial decisions.

First, we examine why publicly traded companies use equity compensation for employees and executives. We discuss how stock grants and restricted shares align incentives, why companies may prefer equity to cash compensation, and what employees should consider when their income and investments become tied to the same company.

Next, we address the tax reality of inheriting a large traditional IRA. With the elimination of the lifetime “stretch” strategy, many beneficiaries now face compressed withdrawals under the 10-year rule. We explore practical approaches to managing the resulting tax burden, including withdrawal timing, income coordination, and portfolio positioning strategies.

Finally, in our From the Field segment, Stephan speaks with Susan Brody, founder of Family Legacy Videos, about how families can document personal stories, preserve values, and create lasting records of family history for future generations.

Stay in touch beyond the podcast:

Newsletter: https://scholarfinancialadvising.com/newsletter

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Submit a question for the show: https://scholarfinancialadvising.com/podcast

Episode 42: Managing Inherited Property, Protecting Physician Wealth, and Inside the Bourbon Market

Scholar Financial Advising, LLC — Mon, 02 Feb 2026 05:00:00 -0500

What should you do when a large portion of your wealth is tied up in illiquid or misunderstood assets?

In this episode, we tackle a listener question from someone who inherited a substantial real estate portfolio, including a primary residence, a vacation home, and rental properties. He walks through how to separate emotional and economic decisions, evaluate real estate as an investment, and avoid treating inherited assets as “default holdings” simply because there’s no urgency to sell.

Next, a question from a neurosurgeon who is becoming increasingly aware that higher income often comes with higher exposure. The discussion focuses on malpractice coverage versus personal liability, the role of umbrella insurance, why liquidity itself is a form of risk management, and why overly complex asset protection structures can create false comfort.

To close the episode, Stephan and Deon are joined by Brian Higgins, master distiller at 1861 Distillery in Georgia, for a conversation on bourbon. Brian explains what actually drives quality long before a label is printed, why age and price are poor shortcuts for value, how the secondary market distorts perception, and how to think differently about drinking, collecting, and investing-adjacent behavior in the bourbon world.

Stay in touch beyond the podcast:

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Episode 39: 529 Planning in an AI World, Raising Grounded Kids, and Understanding REITs

Scholar Financial Advising, LLC — Mon, 12 Jan 2026 05:00:00 -0500

How should families plan for the future when so much feels uncertain?

In this episode, Stephan answers two listener questions that reflect real tradeoffs many high-income families are navigating right now. The first looks at how to approach 529 planning at a time when AI is reshaping education and the job market, and why flexibility matters as much as tax efficiency. The second explores a values-driven concern: how to enjoy lifestyle upgrades like travel and convenience spending without raising kids who feel entitled or disconnected from the effort that built that success.

In the second half of the episode, Stephan is joined by Dr. Stace Sirmans, Professor of Finance at Auburn University, for an educational, no-sales discussion on REITs. Stace breaks down how REITs are defined, how public and private structures differ, common misconceptions around dividends and risk, and what investors often misunderstand about real estate as an asset class.

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Episode 38: Social Security Timing, Home Sale Capital Gains, and Educational Travel with Road Scholar

Scholar Financial Advising, LLC — Mon, 05 Jan 2026 05:00:00 -0500

In this episode of the Scholar Wealth Podcast, we work through two listener questions that reflect the financial and personal tradeoffs many high earners face as they approach retirement.

We begin with a question about Social Security timing. A high-income listener wonders whether it makes sense to claim benefits early and invest them, rather than waiting until age 70, especially given concerns about potential benefit changes and future means testing. Stephan walks through how Social Security actually works, why delayed benefits function more like longevity insurance than an investment, and how to think realistically about policy risk and guaranteed income.

Next, we turn to a housing question from a long-time homeowner in a high appreciation market. After decades of growth, selling a primary residence can trigger a substantial capital gains tax bill, which often causes families to hesitate even when a move makes sense from a lifestyle perspective. We discuss how the primary residence exclusion works, why six-figure tax bills are common in these situations, and how to evaluate tradeoffs between taxes, flexibility, and family priorities.

In our From the Field segment, we’re joined by Kelsey Perri from Road Scholar. We talk about educational travel in retirement, trends in multi-generational and grandparent travel, and why shared experiences and lifelong learning often become a priority once the financial foundation is in place.

Stay in touch beyond the podcast:

Personal Wealth Conference: https://scholarfinancialadvising.com/conference-2026/
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Start your planning journey: https://scholarfinancialadvising.com/welcome
Submit a question for the show: https://scholarfinancialadvising.com/podcast

Episode 37: Qualified Opportunity Zones, IDGTs, and Modern Estate Management

Scholar Financial Advising, LLC — Mon, 29 Dec 2025 05:00:00 -0500

This week on the Scholar Wealth Podcast, we explore three topics that come up as wealth, assets, and complexity grow.

We begin with a listener question from a business owner who recently realized a significant capital gain and is evaluating a Qualified Opportunity Zone investment. Stephan breaks down how QOZs actually work, why tax deferral is no longer the primary benefit, and why the underlying investment must stand on its own before the tax incentives matter.

Next, we turn to Intentionally Defective Grantor Trusts and walk through how these structures are commonly used by closely held business owners to transfer future growth. Stephan explains how IDGTs work in practice, the assumptions they rely on, and the risks that arise when cash flow, growth expectations, or personal spending needs change over time.

In our From the Field segment, Peter Hansen, founder of Sparrow Estate Management, joins us to discuss modern estate management. We talk about staffing models, proactive systems, and how managing a home that has become operationally complex is ultimately about giving families time back and creating consistency across properties.

Stay in touch beyond the podcast:

Newsletter: https://scholarfinancialadvising.com/newsletter
Start your planning journey: https://scholarfinancialadvising.com/welcome
Submit a question for the show: https://scholarfinancialadvising.com/podcast

Episode 34: Buying a €450K Home Abroad, Planning Around Carried Interest, and Building a Wine Collection That Lasts

Scholar Financial Advising, LLC — Mon, 08 Dec 2025 05:00:00 -0500

This week on the Scholar Wealth Podcast, we look at three very different decisions that all require clear thinking and long-term planning. First, Stephan breaks down the financial and family considerations behind buying a €450,000 childhood home in Portugal, including how to separate emotion from economics and how to navigate cross-border tax and management issues.

We then shift to carried interest and what it really means for a principal-level professional. Stephan explains how carry works, why the value is so uncertain, and how to build a financial plan that does not depend on future payouts.

In this week’s From the Field segment, we talk with Walker Strangis of Walker Wine Company about building a fine wine collection with lasting value. He shares practical guidance on buying with purpose, avoiding common mistakes, and thinking about wine as part of a family legacy.

NEXT STEPS

Stay in touch beyond the podcast:

Newsletter: https://scholarfinancialadvising.com/newsletter

Start your planning journey: https://scholarfinancialadvising.com/welcome
Submit a question for the show: https://scholarfinancialadvising.com/podcast

Episode 25: When Spouses Disagree on Legacy Goals, Family Business Concentration Risk, and IRS Audit Insights

Scholar Financial Advising, LLC — Mon, 06 Oct 2025 05:00:00 -0400

This week: two listener questions that highlight the tension between family, finances, and legacy. First, we explore how couples can approach disagreements over whether to spend more now or preserve more wealth for their children. Next, we break down the risks of concentration when a large share of net worth is tied up in a family business, and how to weigh reinvesting versus diversifying.

In our special segment, Stephan is joined by David De Jong, Chair of Stein Sperling’s nationally recognized tax law group. With more than 45 years of experience representing high-net-worth individuals, David shares practical insights on IRS audit triggers, the most common mistakes taxpayers make, and proactive strategies to reduce risk while pursuing effective tax planning.

Have a question for a future episode? Submit it at scholaradvising.com/podcast.

Disclaimer: The information provided in this podcast is for general informational and educational purposes only, and is not intended to constitute financial, investment, or other professional advice. The opinions expressed are those of the hosts and guests and do not necessarily reflect the views of any affiliated organizations. Investing in financial markets involves risk, including the potential loss of principal. Past performance is not indicative of future results. Before making any investment decisions, you should consult with a qualified financial advisor, who can assess your individual financial situation, objectives and risk tolerance. Thanks for listening!

Episode 22: Trusts vs Wills, Senior Living REITs, and a Physician Bonus Playbook

Scholar Financial Advising, LLC — Mon, 15 Sep 2025 05:00:00 -0400

This week’s episode starts with a question from a couple who inherited complications after their parents passed with wills only. Now that their own estate is $5 million, they want to avoid the same outcome for their kids. Stephan explains when it makes sense to move from wills to a trust and the benefits of control, protection, and probate avoidance.

Next, we hear from an investor pitched on a private REIT in senior living communities. With aging demographics and rising demand, it looks like a strong trend—but Stephan walks through the due diligence needed around fees, liquidity, operator experience, and unrealistic assumptions.

Finally, we answer a question from a new attending physician with a $75,000 signing bonus, no debt, and retirement accounts already maxed out. Stephan covers the tax reality and shares how to prioritize liquidity, taxable investing, and long-term flexibility.

In our From the Field segment, we share a heads up that registration is officially open for the 2026 Scholar Personal Wealth Conference in Asheville. More details at scholarfinancialadvising.com/conference-2026/

Have a question for a future episode? Submit it at scholarfinancialadvising.com/podcast

The information provided in this podcast is for general informational and educational purposes only, and is not intended to constitute financial, investment, or other professional advice, the opinions. expressed are those of the hosts and guests and do not necessarily reflect the views of any affiliated organizations. Investing in financial markets involves risk, including the potential loss of principle, past performance is not indicative of future results. Before making any investment decisions, you should consult with a qualified financial advisor, who can assess your individual financial situation, objectives and risk tolerance. Thanks for listening!

Episode 20: Learning Capital for Kids, Tax Loss Harvesting with Direct Indexing, and Hiring a Private Chef

Scholar Financial Advising, LLC — Mon, 01 Sep 2025 05:00:00 -0400

In this episode of the Scholar Wealth Podcast, Stephan Shipe answers three listener questions that highlight the real-world decisions families face at different stages of wealth.

First, we look at a parent’s dilemma when their 23-year-old daughter wants to invest $50,000 in crypto. How can families encourage curiosity and independence in investing while setting guardrails to protect long-term wealth?

Next, we explore whether direct indexing is worth the complexity for a $6 million taxable portfolio, especially for someone already donating appreciated stock to a donor-advised fund. Stephan breaks down how direct indexing compares to ETFs and mutual funds, and when it makes sense as a tax loss harvesting strategy.

Finally, we examine the financial logistics of hiring a private chef at a family’s Nantucket home held in trust. From payroll and liability issues to whether the expense can be covered by the trust or should be split among family members, Stephan outlines the key considerations for aligning lifestyle spending with long-term planning.

And in our Term of the Day segment, we unpack QSBS — Qualified Small Business Stock — a powerful but often overlooked tax planning opportunity for entrepreneurs and early investors.

Have a question for a future episode? Submit it at scholarfinancialadvising.com/podcast.

Episode 18: When to Sell, When to Hedge, and When to Start Your Second Act

Scholar Financial Advising, LLC — Mon, 18 Aug 2025 05:00:00 -0400

In this episode of the Scholar Wealth Podcast, we tackle big wealth strategy questions. First, Stephan answers whether now is the right time to sell a gold coin collection worth $250,000, with gold prices at record highs. We cover how to value a gold collection, when to sell gold coins, and how to identify a fair auction house commission versus being taken advantage of.

Next, we explore currency diversification for high-net-worth investors, including whether moving several million into foreign currencies or international bonds is a smart hedge against US dollar risk and banking system instability. Stephan shares the pros and cons of international bond funds, currency hedging strategies, and proportional allocations for large portfolios.

Finally, in our Money Masters segment, special guest Byron shares his journey as a successful DIY investor—how he built confidence in managing his own investments, reached financial independence, and reinvented himself in retirement. It’s a conversation about second-act planning, wealth protection, and making work optional.

Disclosures: The guest on this podcast was a client of Scholar Financial Advising as of the date of recording, and was not compensated for their time. Nothing conveyed by the guest should be construed as a testimonial or endorsement of Scholar Financial Advising, and their experience as an investor or a client may not be representative of all investor or client experiences. The information provided in this podcast is for general informational and educational purposes only, and is not intended to constitute financial, investment, or other professional advice, the opinions. expressed are those of the hosts and guests and do not necessarily reflect the views of any affiliated organizations. Investing in financial markets involves risk, including the potential loss of principle, past performance is not indicative of future results. Before making any investment decisions, you should consult with a qualified financial advisor, who can assess your individual financial situation, objectives and risk tolerance.

Episode 15: Fractional Jets, Option Exercises, and Estate Fairness: Financial Planning at the Next Level

Scholar Financial Advising, LLC — Mon, 28 Jul 2025 05:00:00 -0400

This week’s episode starts with a question from a family debating whether to keep their fractional jet ownership or buy a midsize jet outright. Stephan walks through the tax benefits, depreciation rules, and hidden costs that factor into the decision—and why the math isn’t as simple as cost per hour.

Next, we hear from an executive with a large stock option package who wants to exercise wisely without triggering an unnecessary tax bill.

Then, we answer a question from a parent who wants to leave more to one child without creating family tension. We talk through how to use gifts, trusts, and legacy letters to balance fairness and support.

Finally, in this week’s Advisor Red Flags segment, Stephan breaks down why promises to make your stock options “tax-free” are a warning sign.

Have a question for a future episode? Submit it at scholarfinancialadvising.com/podcast.

Episode 14: Dividing, Inheriting, and Starting Fresh: Smart Moves After Life’s Turning Points

Scholar Financial Advising, LLC — Mon, 21 Jul 2025 05:00:00 -0400

We kick off this week's episode with a question from a divorce attorney who listens to help his clients make smarter financial decisions. Stephan shares what really matters when dividing assets like real estate, retirement accounts, and taxable investments... and why equal isn’t always equitable.

Next, we hear from a physician couple in their late 30s who just paid off student loans and want to know what’s next.

Then, we tackle a listener question about inheriting a taxable brokerage account. What does a step-up in basis mean, and how do you decide whether to hold or sell the investments?

Finally, in this week’s Myth or Money, Stephan takes on the idea that "I'm too young to worry about retirement."

Have a question for a future episode? Submit it at scholarfinancialadvising.com/podcast.

Episode 1: Launching the Scholar Wealth Podcast

Scholar Financial Advising, LLC — Mon, 21 Apr 2025 07:00:00 -0400

In this first episode of the Scholar Wealth Podcast, host Stephan Shipe introduces himself, shares the story behind the show, and outlines what listeners can expect each week. With a PhD in finance, years of academic research, and experience advising high-net-worth families, Stephan explains why this podcast was created: to provide clear, expert insights for families facing complex wealth challenges.

From multi-generational legacy planning to executive compensation, business exits, philanthropy, and beyond, this podcast is built for those who want to go deeper than the basics. Stephan also introduces the Scholar Wealth Network, a community designed to connect families with resources, education, and expert perspectives.

Tune in to hear the mission behind the podcast and how you can get involved by submitting your own questions and joining the conversation.