app03 Mon, 21 Sep 2026 15:50:57 +0000 Fireside (https://fireside.fm) The Scholar Wealth Podcast - Episodes Tagged with “Intrafamily Loans” https://sfa-podcast.fireside.fm/tags/intrafamily%20loans Mon, 21 Sep 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 75: Selling Your Business Beyond the Earnout, Family Loans and the IRS, Counterfeit Wine https://sfa-podcast.fireside.fm/75 1b057db1-3960-498a-9e62-2ca0d0dc89be Mon, 21 Sep 2026 05:00:00 -0400 Scholar Financial Advising, LLC full Scholar Financial Advising, LLC This week on the Scholar Wealth Podcast, Stephan takes on two listener questions and is joined in From the Field by Maureen Downey, founder of Chai Consulting and one of the foremost independent authorities on counterfeit wine. The first listener is preparing to sell his business and, after hearing our earlier earnout episode, wants to know what else in a deal structure can cost sellers at close. The second is a set of parents hoping to help their son and daughter-in-law buy their first home in an expensive market through a below-market family loan, and wants to understand what the IRS actually allows. Maureen walks through how fake wine ends up in top cellars, why an estimated one in five bottles of fine wine on the secondary market is counterfeit, and how The Chai Method authentication process works. 40:43 no <p>A listener preparing to sell his business writes in after our earlier episode on earnouts. He now understands that piece of the deal, but wants to know what else could cost him at close. Stephan walks through the parts of a transaction that get less attention than the headline number: rollover equity, escrow holdbacks, working capital true-ups, and reps and warranties. Each one moves the number the seller actually keeps, and each one is negotiable if you know it's there before you sign the LOI.</p> <p>Next, a set of parents wants to help their son and daughter-in-law buy their first home in a market where the math no longer works on a conventional mortgage. They're considering a family loan at a rate well below what the bank would offer. Stephan covers what the IRS requires to keep a family loan from being reclassified as a gift, how the Applicable Federal Rate sets the floor, and the family dynamics worth thinking through before the money moves, especially when a spouse is on the other side of the note.</p> <p>Then, in our From the Field segment, we're joined by Maureen Downey, founder of Chai Consulting and one of the foremost independent authorities on counterfeit wine. Maureen has advised the FBI and DOJ on major wine fraud cases and developed The Chai Method, the authentication process used by top auction houses, insurers, and private collectors. She explains why an estimated 20 percent of fine wine on the secondary market is counterfeit, how fakes end up in some of the most respected cellars in the world, and what collectors and their advisors should be doing before writing the next check.</p> <p>Stay in touch beyond the podcast:</p> <p>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>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! </p> selling a business, business exit, deal structure, earnout, rollover equity, escrow holdback, working capital adjustment, reps and warranties, letter of intent, LOI, private equity sale, seller financing, what to negotiate when selling your business, hidden costs of selling a business, what happens after signing an LOI, purchase price versus net proceeds, family loan, intrafamily loan, applicable federal rate, AFR, IRS gift tax, gifting to children, helping adult children buy a home, below market interest rate loan, family mortgage, promissory note, gift tax exclusion, intrafamily loan rules, gift or loan IRS rules, helping son buy first home, counterfeit wine, fake wine, wine fraud, wine authentication, Maureen Downey, Chai Consulting, The Chai Method, fine wine collecting, wine investment, wine cellar authentication, bordeaux counterfeits, burgundy fraud, secondary wine market, wine auction fraud, provenance in fine wine, luxury asset authentication, Scholar Wealth Podcast, Stephan Shipe, Scholar Financial Advising, flat fee financial advisor, fiduciary advisor, wealth management, financial planning, independent financial advisor, financial podcast A listener preparing to sell his business writes in after our earlier episode on earnouts. He now understands that piece of the deal, but wants to know what else could cost him at close. Stephan walks through the parts of a transaction that get less attention than the headline number: rollover equity, escrow holdbacks, working capital true-ups, and reps and warranties. Each one moves the number the seller actually keeps, and each one is negotiable if you know it's there before you sign the LOI.

Next, a set of parents wants to help their son and daughter-in-law buy their first home in a market where the math no longer works on a conventional mortgage. They're considering a family loan at a rate well below what the bank would offer. Stephan covers what the IRS requires to keep a family loan from being reclassified as a gift, how the Applicable Federal Rate sets the floor, and the family dynamics worth thinking through before the money moves, especially when a spouse is on the other side of the note.

Then, in our From the Field segment, we're joined by Maureen Downey, founder of Chai Consulting and one of the foremost independent authorities on counterfeit wine. Maureen has advised the FBI and DOJ on major wine fraud cases and developed The Chai Method, the authentication process used by top auction houses, insurers, and private collectors. She explains why an estimated 20 percent of fine wine on the secondary market is counterfeit, how fakes end up in some of the most respected cellars in the world, and what collectors and their advisors should be doing before writing the next check.

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

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!

]]> A listener preparing to sell his business writes in after our earlier episode on earnouts. He now understands that piece of the deal, but wants to know what else could cost him at close. Stephan walks through the parts of a transaction that get less attention than the headline number: rollover equity, escrow holdbacks, working capital true-ups, and reps and warranties. Each one moves the number the seller actually keeps, and each one is negotiable if you know it's there before you sign the LOI.

Next, a set of parents wants to help their son and daughter-in-law buy their first home in a market where the math no longer works on a conventional mortgage. They're considering a family loan at a rate well below what the bank would offer. Stephan covers what the IRS requires to keep a family loan from being reclassified as a gift, how the Applicable Federal Rate sets the floor, and the family dynamics worth thinking through before the money moves, especially when a spouse is on the other side of the note.

Then, in our From the Field segment, we're joined by Maureen Downey, founder of Chai Consulting and one of the foremost independent authorities on counterfeit wine. Maureen has advised the FBI and DOJ on major wine fraud cases and developed The Chai Method, the authentication process used by top auction houses, insurers, and private collectors. She explains why an estimated 20 percent of fine wine on the secondary market is counterfeit, how fakes end up in some of the most respected cellars in the world, and what collectors and their advisors should be doing before writing the next check.

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

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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