web01.fireside.fm Wed, 15 Apr 2026 03:42:45 -0500 Fireside (https://fireside.fm) The Scholar Wealth Podcast - Episodes Tagged with “Multigenerational Travel Planning” https://sfa-podcast.fireside.fm/tags/multigenerational%20travel%20planning Mon, 05 Jan 2026 05:00:00 -0500 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 38: Social Security Timing, Home Sale Capital Gains, and Educational Travel with Road Scholar https://sfa-podcast.fireside.fm/38 5f7802a3-438f-4c7f-a3b1-4c29462255e7 Mon, 05 Jan 2026 05:00:00 -0500 Scholar Financial Advising, LLC full Scholar Financial Advising, LLC In this episode, we answer two listener questions that highlight common retirement planning tradeoffs. We discuss Social Security timing for high earners, capital gains considerations when selling a long-held primary residence, and how families think about prioritizing meaningful experiences through educational travel with Road Scholar. 31:12 no 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/ Newsletter: https://scholarfinancialadvising.com/newsletter Start your planning journey: https://scholarfinancialadvising.com/welcome Submit a question for the show: https://scholarfinancialadvising.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! social security timing, when to claim social security, claim social security early or wait, social security for high earners, social security delay to age 70, invest social security benefits, capital gains tax on home sale, primary residence capital gains exclusion, selling a home capital gains tax, high appreciation home capital gains, california home sale capital gains tax, net investment income tax on home sale, retirement tax planning, retirement planning strategies, tax planning for retirees, moving in retirement tax considerations, downsizing in retirement taxes, multigenerational travel retirement, educational travel in retirement, road scholar travel, retirement lifestyle planning, planning for the second act 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/
Newsletter: https://scholarfinancialadvising.com/newsletter
Start your planning journey: https://scholarfinancialadvising.com/welcome
Submit a question for the show: https://scholarfinancialadvising.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!

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

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