Displaying items 1-10 of 26 in total of The Scholar Wealth Podcast with the tag "gifting strategies".
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Episode 80: HYSA, Roth Tilt, Gold, and Gifting: Five Finance Debates
October 26th, 2026 | 39 mins 49 secs
estate planning, financial literacy, gifting strategies, inflation planning, inheritance planning, portfolio rebalancing, retirement planning, tax planning, trust strategies
Noah Lewis and Evan Mills face off on five of the contested questions in personal finance: HYSA vs brokerage for emergency funds, value vs growth in a Roth IRA, VGIT vs BIV for the bond sleeve, equities vs gold as an inflation hedge, and direct gifting vs gifting into a trust.
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Episode 75: Selling Your Business Beyond the Earnout, Family Loans and the IRS, Counterfeit Wine
September 21st, 2026 | 40 mins 43 secs
asset protection, business exit strategy, business sale deal structure, collectibles authentication, family gifting strategies, gifting strategies, inheritance planning, intrafamily loans, liquidity event, tax planning, wine collecting
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.
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Episode 74: Cash Balance Plans for High-Earning Physicians, Building a System for Lumpy Income, and Trust Provisions for Adult Kids
September 14th, 2026 | 17 mins 50 secs
adult children inheritance, cash balance plans, contingency attorney finance, estate planning, financial independence, gifting strategies, incentive trusts, inheritance planning, lumpy income planning, physician finance, retirement planning, tax planning, trust strategies
Stephan tackles three listener questions: whether a high-earning locums anesthesiologist should stack a $200K cash balance plan on top of a maxed solo 401(k), how a contingency attorney with wildly lumpy income and no plans to retire should build a real financial system, and what trust provisions preserve adult kids' drive without controlling from the grave.
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Episode 72: The Uninterested Heir, Earnout Reality Check, and Hiring a Nanny
August 31st, 2026 | 28 mins 42 secs
business exit strategy, business sale earnout planning, financial literacy, gifting strategies, gifting to adult children, household staff, inheritance planning, liquidity event, nanny, tax planning
A self-managed investor asks whether his 28-year-old son should use a wealth manager. A business owner selling on an earnout tries to figure out how much of it to plan around. And Stephanie Fornaro of Hello Nanny on the mistakes families make when they hire household support.
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Episode 70: The Boulder Home Decision, What "Complex" Really Means, and Generational Wealth Stewardship with Lisa McCurdy
August 17th, 2026 | 33 mins 48 secs
charitable giving, concentration risk, estate planning, estate tax exemption, gifting strategies, inheritance planning, legacy and family stewardship, sbloc, tax planning, trust strategies
Stephan works through two listener questions this week. First, a couple weighing three ways to buy a $2.8 million second home in Boulder and disagreeing about whether an SBLOC belongs on the table. Then, a listener with a $35 million net worth concentrated 80 percent in one stock who wants to know why every advisor he meets calls his situation "complex" when it feels pretty simple from where he sits. In From the Field, legacy planning attorney Lisa McCurdy joins to explain why the human side of estate work, not the paperwork, is what determines whether a plan actually holds up across generations.
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Episode 66: The $800K CPA Gap, Negotiating Away From Unvested RSUs, and Money Masters with Mike
July 20th, 2026 | 34 mins 40 secs
charitable giving, deferred compensation, endowment portfolio, estate planning, executive compensation, financial independence, financial literacy, generational wealth transfer, gifting strategies, high income tax strategy, inheritance planning, retirement planning, retirement transition planning, stock option exercise, tax planning
A high earner realizing his CPA is filing history rather than shaping strategy, a professional weighing a competitor offer with $2.8M in unvested RSUs and deferred comp on the line, and Money Masters with Mike on retiring at 56, building an endowment-style portfolio, and passing it on with intention.
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Episode 65: IPO Access, Dynasty Trusts, and Bitcoin Arbitrage Funds
July 13th, 2026 | 26 mins 11 secs
alternative investments, concentration risk, cryptocurrency investing, dynasty trusts, estate planning, financial independence, gifting strategies, inheritance planning, ipo planning, tax planning, trust strategies
Three listener questions this week: a Bay Area tech executive working out how to get real access to IPOs after landing only 13% of his SpaceX allocation, a family pressure testing whether the ongoing costs of an irrevocable dynasty trust actually pencil out for long-horizon private investments, and a listener weighing whether Bitcoin arbitrage funds are as market neutral as they appear on paper.
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Episode 64: Gifting at 88, Deferred Comp Defaults, and 100-Year Families
July 6th, 2026 | 40 mins 31 secs
100-year family enterprises, deferred comp elections, deferred compensation, estate planning, executive compensation, family business, financial literacy, gifting strategies, inheritance planning, lifetime gifting to grandchildren, retirement planning, step-up in basis, tax planning, three-generation myth
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.
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Episode 61: Preparing the Spouse Who Doesn't Manage the Money, When Vacation Rental Income Disappears, and Preparing Heirs with Jessica McGawley
June 15th, 2026 | 29 mins 9 secs
asset protection, estate planning, family business, family governance, family wealth transfer, financial literacy, gifting strategies, inheritance planning, real estate investing, retirement planning, spousal financial planning, trust strategies, vacation rental
A wife who has managed every dollar of her family's $19 million for thirty years faces the reality that her husband doesn't know where any of it is. A couple at 63 lose their beach house rental income overnight when a zoning change kills VRBO on their street. And in From the Field, Jessica McGawley of Dallington joins us on preparing the next generation for wealth, not just preparing the wealth for them.
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Episode 59: Family Property Tax Traps, I Bonds vs. Treasury Ladders, and Rethinking the Prenup with Aaron Thomas
June 1st, 2026 | 40 mins 33 secs
asset protection, business exit strategy, cash management, corporate cash strategy, estate planning, family property tax, gifting strategies, i bonds, inflation planning, liquidity event, prenuptial agreements, real estate investing, tax planning, treasury laddering, vacation rental
Three properties, family use, and a CPA raising tax flags. Twelve million in cash and the I bonds versus Treasury ladder debate. Then Aaron Thomas, founder of Prenups.com and one of the country's leading family law attorneys, joins Stephan to reframe prenuptial agreements as foundational tools for clarity and alignment, not defensive instruments.