app01 Fri, 07 Aug 2026 11:58:23 +0000 Fireside (https://fireside.fm) The Scholar Wealth Podcast - Episodes Tagged with “Step Up In Basis” https://sfa-podcast.fireside.fm/tags/step-up%20in%20basis Mon, 06 Jul 2026 05:00:00 -0400 The Scholar Wealth Podcast delivers clear, expert insights into the financial decisions that shape the lives of successful individuals and families of significant means. Every Monday morning, our team of highly credentialed financial advisors brings clarity to complex wealth challenges—through listener questions, conversations with subject-matter experts, and real stories of financial journeys. This isn’t generic guidance or mass-market advice. It’s financial clarity for people with more at stake: physicians navigating equity compensation, entrepreneurs preparing for business exits, and families stewarding multigenerational wealth. Each episode offers trusted guidance, grounded in experience and fiduciary care. 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 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. en-us episodic Complex Wealth Questions. Expert Answers. Scholar Financial Advising, LLC The Scholar Wealth Podcast delivers clear, expert insights into the financial decisions that shape the lives of successful individuals and families of significant means. Every Monday morning, our team of highly credentialed financial advisors brings clarity to complex wealth challenges—through listener questions, conversations with subject-matter experts, and real stories of financial journeys. This isn’t generic guidance or mass-market advice. It’s financial clarity for people with more at stake: physicians navigating equity compensation, entrepreneurs preparing for business exits, and families stewarding multigenerational wealth. Each episode offers trusted guidance, grounded in experience and fiduciary care. 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 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. no finance, investing, high-income, tax strategy, personal finance, wealth management podcast, high net worth financial planning, fiduciary financial advice, physician finance podcast, estate planning podcast, investment strategy podcast, tax planning podcast, business exit strategy podcast, financial planning for high net worth families, podcast for physicians with equity compensation, tax strategies for entrepreneurs selling a business, multigenerational wealth planning podcast, personal finance stories high net worth, fiduciary advisors podcast, deferred compensation planning podcast, portfolio rebalancing advice podcast, high net worth investing, ultra high net worth wealth strategies, gifting and legacy planning, private equity and alternative investments, liquidity event financial planning, trust and estate strategies, financial independence for entrepreneurs, expert interviews on wealth management Scholar Financial Advising, LLC stephan@scholarfinancialadvising.com Episode 64: Gifting at 88, Deferred Comp Defaults, and 100-Year Families https://sfa-podcast.fireside.fm/64 acf25c2d-14d3-47cf-8922-7fda8dd743e7 Mon, 06 Jul 2026 05:00:00 -0400 Scholar Financial Advising, LLC full Scholar Financial Advising, LLC An 88-year-old mother with $6 million in a brokerage account of embedded gains wants to gift to her grandchildren now, and Stephan works through the tradeoff between lifetime gifting and the step-up at death, the tools that solve the problem without sacrificing basis, and why the honest answer at 88 is rarely more complicated than annual exclusions and direct payments. Then a 51-year-old executive defaulting to lump-sum-at-separation on his deferred comp elections gets a full walkthrough of what's actually at stake — Section 409A irrevocability, credit risk, the tax cliff at separation, and how installment options and in-service distributions coordinate with the years ahead. In From the Field, organizational psychologist Dennis Jaffe joins the show to share what he learned from interviewing 100 families across 22 countries that have thrived past their third generation, why the "three-generation curse" is largely a myth, and how successful families evolve from a single entrepreneur into a cooperative community across generations. 40:31 no <p>An 88-year-old mother wants to start gifting to her grandchildren now, while she's still around to see it. The complication is fifty years of embedded gains in one brokerage account, and a question about whether lifetime gifting quietly sacrifices the step-up at death. Stephan works through the textbook answer, the realistic answer, and where the two diverge.</p> <p>A 51-year-old executive has been defaulting to lump-sum-at-separation on his deferred comp elections every November without thinking much about it. With another decade of work ahead and a meaningful balance accruing, this segment walks through what's actually at stake, why the default is almost always the worst choice, and what to evaluate before this year's window closes.</p> <p>Then in From the Field, Dennis Jaffe joins the show. Dennis is an organizational psychologist and one of the world's leading researchers on multigenerational family enterprises. After interviewing 100 families across 22 countries that have thrived past their third generation, Dennis shares what actually makes wealth and values endure across generations, why the ""three-generation curse"" is largely a myth, and how successful families evolve from a single entrepreneur into a cooperative community.</p> <p>Stay in touch beyond the podcast:<br> Newsletter: <a href="https://scholarfinancialadvising.com/newsletter" rel="nofollow noopener">https://scholarfinancialadvising.com/newsletter</a><br> Start your planning journey: <a href="https://scholarfinancialadvising.com/welcome" rel="nofollow noopener">https://scholarfinancialadvising.com/welcome</a><br> Submit a question for the show: <a href="https://scholarfinancialadvising.com/podcast" rel="nofollow noopener">https://scholarfinancialadvising.com/podcast</a></p> <p>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!</p> step-up in basis, gifting appreciated stock, lifetime gifts vs step-up, gifting to grandchildren, annual exclusion gifts, direct tuition payment, 529 superfunding, cost basis carryover, estate tax exemption, state estate tax, deferred compensation, deferred comp elections, non-qualified deferred compensation, NQDC, Section 409A, lump sum vs installments, deferred comp distribution options, in-service distributions, executive compensation planning, unsecured creditor risk, family business succession, multigenerational wealth, 100-year family enterprises, third generation problem, family governance, family office, Dennis Jaffe, Borrowed from Your Grandchildren, next generation wealth transfer, family enterprise research An 88-year-old mother wants to start gifting to her grandchildren now, while she's still around to see it. The complication is fifty years of embedded gains in one brokerage account, and a question about whether lifetime gifting quietly sacrifices the step-up at death. Stephan works through the textbook answer, the realistic answer, and where the two diverge.

A 51-year-old executive has been defaulting to lump-sum-at-separation on his deferred comp elections every November without thinking much about it. With another decade of work ahead and a meaningful balance accruing, this segment walks through what's actually at stake, why the default is almost always the worst choice, and what to evaluate before this year's window closes.

Then in From the Field, Dennis Jaffe joins the show. Dennis is an organizational psychologist and one of the world's leading researchers on multigenerational family enterprises. After interviewing 100 families across 22 countries that have thrived past their third generation, Dennis shares what actually makes wealth and values endure across generations, why the ""three-generation curse"" is largely a myth, and how successful families evolve from a single entrepreneur into a cooperative community.

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

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!

]]> An 88-year-old mother wants to start gifting to her grandchildren now, while she's still around to see it. The complication is fifty years of embedded gains in one brokerage account, and a question about whether lifetime gifting quietly sacrifices the step-up at death. Stephan works through the textbook answer, the realistic answer, and where the two diverge.

A 51-year-old executive has been defaulting to lump-sum-at-separation on his deferred comp elections every November without thinking much about it. With another decade of work ahead and a meaningful balance accruing, this segment walks through what's actually at stake, why the default is almost always the worst choice, and what to evaluate before this year's window closes.

Then in From the Field, Dennis Jaffe joins the show. Dennis is an organizational psychologist and one of the world's leading researchers on multigenerational family enterprises. After interviewing 100 families across 22 countries that have thrived past their third generation, Dennis shares what actually makes wealth and values endure across generations, why the ""three-generation curse"" is largely a myth, and how successful families evolve from a single entrepreneur into a cooperative community.

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

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 14: Dividing, Inheriting, and Starting Fresh: Smart Moves After Life’s Turning Points https://sfa-podcast.fireside.fm/14 f83bcb0a-ab27-448c-901a-76ef899bfa2b Mon, 21 Jul 2025 05:00:00 -0400 Scholar Financial Advising, LLC full Scholar Financial Advising, LLC From divorce settlements to post-inheritance decisions to finally being debt-free—life’s transitions come with big financial questions. In this episode, we answer listener questions about dividing marital assets, what to do after inheriting a $1.2M brokerage account, and how two physicians can reset their financial plan after paying off student loans. Plus, in Myth or Money, we bust the idea that you're ever too young to plan for retirement. 22:17 no <p>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.</p> <p>Next, we hear from a physician couple in their late 30s who just paid off student loans and want to know what’s next. </p> <p>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?</p> <p>Finally, in this week’s Myth or Money, Stephan takes on the idea that "I'm too young to worry about retirement."</p> <p>Have a question for a future episode? Submit it at scholarfinancialadvising.com/podcast.</p> dividing marital assets, divorce and finances, inheritance planning, inherited brokerage account, step-up in basis, post-inheritance strategy, financial planning after debt, financial reset for physicians, student loan payoff planning, physician financial advice, asset division strategy, pre-tax vs after-tax assets, real estate vs cash in divorce, financial planning after divorce, taxable investment decisions, portfolio rebalancing after inheritance, retirement planning in your 30s, too young to plan for retirement, financial transitions, managing windfalls, equity vs equality in asset division, financial planning for doctors, financial planning, Q&A podcast, wealth building after student loans, estate planning tips, capital gains tax inheritance, myth or money 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.

]]> 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.

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