Displaying items 1-10 of 12 in total of The Scholar Wealth Podcast with the tag "charitable giving".
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Episode 58: The $10M Restlessness, AI IPO Stock Decisions, and Heirloom Construction
May 25th, 2026 | 37 mins 52 secs
charitable giving, concentrated stock, concentration risk, executive compensation, financial independence, ipo planning, iso tax planning, liquidity event, luxury residential construction, pre-ipo planning, retirement planning, stock option exercise, tax planning
A business owner in his mid-forties with ten million saved asks why every financial milestone has failed to feel like arrival, and what mistakes people in his position tend to make. Then a software engineer at one of the major AI companies heading toward a historic IPO asks how to plan around fifteen million in pre-IPO equity, including ISOs, AMT exposure, and the holding periods that unlock long-term capital gains. In From the Field, we are joined by Matt Lutz, Managing Director of Flatwater Homes, for a conversation about luxury residential construction, from underground garages to glass-walled natatoriums.
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Episode 57: Q&A Speed Round with Noah and Evan: AI Investing, Living Off Dividends, 529-to-Roth, and More
May 18th, 2026 | 25 mins 28 secs
bond investing, charitable giving, concentration risk, education funding, estate planning, gifting strategies, inflation planning, international planning, investment strategy, retirement planning, tax planning, trust strategies
A Q&A speed round with Associate Financial Advisors Noah Lewis and Evan Mills, tackling eight listener questions across investing and planning. Topics include AI as a structural shift, international allocation, dividends versus selling shares, gifting tuition to grandkids, BIV versus money markets, I-bonds and TIPS, the 529-to-Roth rollover under SECURE 2.0, and charitable remainder trusts versus donor advised funds.
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Episode 53: Structured Family Support, Cash Balance Plans, and Hiring a Private Chef
April 20th, 2026 | 31 mins 52 secs
adult child financial support, asset protection, business exit strategy, cash balance plan, charitable giving, defined benefit plan, domestic staff hiring, estate planning, family business, family gifting strategy, financial independence, gifting strategies, inheritance planning, private chef placement, retirement contribution stacking, retirement planning, solo 401k, tax planning
A listener asks how to structure financial support for an adult child in a way that builds accountability rather than dependence. Then, a consultant explores whether layering a cash balance plan on top of a solo 401(k) makes sense, and what the long-term funding commitment actually looks like. Chris Demaillet, founder of Montclair Chef, joins From the Field to discuss what families need to know before hiring a private chef.
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Episode 51: Rachel Cruze of The Ramsey Show on Raising Money-Smart Kids, DAFs vs. Private Foundations, and Getting Into Alternatives
April 6th, 2026 | 36 mins 25 secs
alternative investments, charitable giving, donor-advised funds, estate planning, family business, family philanthropy, financial literacy, generational wealth transfer, gifting strategies, inheritance planning, parenting and money, private equity investment, private foundations, real estate investing, rental property, tax planning, third-generation wealth, trust strategies
Rachel Cruze, author and co-host of The Ramsey Show, joins us to talk about how financial values are formed, passed down, and sometimes lost across generations. We also look at when a private foundation makes more sense than a donor-advised fund for a family giving $200,000 a year, and whether rental real estate is a smart entry point into alternatives — or just trading one set of risks for another.
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Episode 45: Family Travel Fairness, STR Bonus Depreciation, and Digital Risk Management
February 23rd, 2026 | 37 mins 26 secs
asset protection, bonus depreciation, charitable giving, cybersecurity, family dynamics, financial literacy, gifting strategies, intergenerational wealth, real estate investing, short-term rentals, tax planning, vacation rental
In this episode, we explore how complexity shows up in family dynamics, tax strategy, and digital risk. We discuss how parents can navigate lifestyle differences among adult children without falling into the reallocation trap, unpack how bonus depreciation for short-term rentals actually works under the One Big Beautiful Bill, and close with a From the Field conversation on modern cybersecurity risks facing high-profile families and family offices.
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Episode 41: Choosing Charitable Impact, Wash Sale Rules, and Business Valuation in Practice
January 26th, 2026 | 38 mins 36 secs
business exit strategy, business valuation, charitable giving, charitable impact, estate planning, family business, nonprofit evaluation, portfolio rebalancing, tax loss harvesting, tax planning, wash sale rules
In this episode, we explore how financial decisions can still feel complicated even when the numbers clearly work. The conversation covers how to choose impactful charitable giving without an existing connection, how wash sale rules show up in real-world portfolios, and a practical discussion with Mike Blake on how business valuations actually work in practice.
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Episode 32: Irish-Domiciled ETFs, 2026 IPS Refresh, and Luxury Holiday Design
November 24th, 2025 | 25 mins 34 secs
charitable giving, donor-advised funds, estate planning, expat investing, family business, family governance, financial independence, financial literacy, international planning, ips updates, irish etfs, luxury holiday décor, seasonal planning, tax planning
This episode explores three sides of global wealth management and seasonal lifestyle planning. Stephan Shipe, Ph.D., CFA, CFP®, explains how non-U.S. residents can access index-fund diversification through Irish-domiciled ETFs, then breaks down what modern family offices should include in a 2026 Investment Policy Statement refresh. In our From the Field segment, holiday designer Christine Mango shares how luxury families create festive, elegant spaces for the season.
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Episode 29: CRUT Strategies, Contingency Fee Windfalls, and Protecting Valuable Collections
November 3rd, 2025 | 29 mins 31 secs
art insurance, asset protection, charitable giving, charitable remainder trusts, contingency attorneys, cruts, donor-advised funds, financial literacy, fine art protection, legal windfalls, liquidity event, liquidity management, real estate investing, real estate sales, risk management, tax planning, trust strategies, uneven income planning, valuable collections
This episode examines three sides of wealth protection: how to use a charitable remainder unitrust (CRUT) when selling appreciated real estate, how contingency attorneys should plan after a major payout, and how to safeguard valuable art and collectibles with Anne Rappa of Marsh McLennan Agency.
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Episode 23: SLAT Adjustments, Family Philanthropy, and Spotting Ponzi Schemes
September 22nd, 2025 | 33 mins 57 secs
alternative investment risks, asset protection, balancing family giving priorities, charitable giving, cost-of-living trust adjustments, donor-advised fund strategy, due diligence for private investments, estate planning, family foundation governance, financial literacy, gifting strategies, heirs financial literacy, hems trust provisions, inflation planning, irrevocable trust modification, legacy planning strategies, next-gen philanthropy, ponzi scheme red flags, ponzi schemes, real estate syndication fraud, slat distribution flexibility, spotting investment fraud, trust strategies
Two complex questions for high-net-worth families: 1) How much flexibility should couples build into SLAT distributions as living costs rise? 2) How can families balance decades-long charitable commitments with next-generation priorities? Plus, a From the Field interview with attorney Daniel Gielchinsky, who shares the red flags he’s seen in Ponzi schemes and fraudulent investment pitches.
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Episode 20: Learning Capital for Kids, Tax Loss Harvesting with Direct Indexing, and Hiring a Private Chef
September 1st, 2025 | 22 mins 44 secs
charitable giving, concentration risk, crypto investing, dafs, direct indexing, estate planning, financial independence, financial literacy, gifting strategies, inheritance planning, learning capital, market timing, portfolio rebalancing, qsbs, tax loss harvesting, tax planning, trust strategies
In this episode, we answer listener questions about setting boundaries around “learning capital” when a child wants to invest trust assets in crypto, weighing the benefits of direct indexing for tax loss harvesting in a $6 million taxable portfolio, and handling the financial logistics of hiring a private chef for a family-owned summer residence. Plus, our Term of the Day segment breaks down QSBS — Qualified Small Business Stock — and why it can be such a powerful tax planning opportunity for entrepreneurs.