Displaying items 1-10 of 23 in total of The Scholar Wealth Podcast with the tag "real estate investing".
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Episode 81: Buying a Home Owned by a Pension, Three Homes and No Budget, Leaving New York for Florida
November 2nd, 2026 | 20 mins 20 secs
estate planning, inheritance planning, international planning, lumpy partner income, multi-property budgeting, new york residency change, pension-owned real estate, real estate investing, retirement planning, state tax relocation, tax planning, trust strategies
Three listener questions on homes and the planning problems that come with them. A relocation buyer evaluates a house held in a seller’s defined benefit plan through Equity Trust Company. A family with three homes and quarterly partner distributions tries to build a budget that holds up. And a $2.1 million New York earner moves to Palm Beach while keeping real ties to the Northeast.
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Episode 77: The Fed Cut and the Bond Market, Physical Gold as Risk Management, and the Commercial Real Estate Refinancing Wall
October 5th, 2026 | 38 mins 33 secs
bond market, commercial real estate, federal reserve, financial independence, gold, inflation planning, market commentary, portfolio rebalancing, real estate investing, scholar big picture
Our quarterly Scholar Big Picture with Dr. Deon Strickland runs the full episode. Deon and Stephan cover the Fed's recent cut and how Kevin Warsh has positioned the bond market, whether long bonds start to make sense at higher yields, the fiscal math behind six percent deficits, a real shift in Deon's thinking on physical gold as risk management, the commercial real estate refinancing wall, and the tokenization of securities as the silver lining worth watching.
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Episode 76: Trustee Crime Insurance, Paying 1% for Alts Access, and NYC Real Estate with Ashley Reidy Quinn
September 28th, 2026 | 37 mins 35 secs
asset protection, corporate co-trustee structure, estate planning, inheritance planning, nyc real estate market, pied-à-terre tax, private equity investment, private investment access fees, real estate investing, trust strategies, trustee crime insurance
Trustee crime insurance and the structural questions to ask first, whether 1% is fair for advisor-brokered alts access, and Ashley Reidy Quinn of Christie's International Real Estate New York on a flat NYC market driven almost entirely by cash.
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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.
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Episode 54: Mortgages, Trusts, Hedge Funds, and More: Live Q&A from Our Annual Conference
April 27th, 2026 | 35 mins 10 secs
estate planning, financial literacy, gifting strategies, incentive stock options, inheritance planning, live q&a, real estate investing, real estate syndication, retirement planning, stock option exercise, talking to kids about money, tax planning, trust distribution, trust strategies
This week, we're bringing you something a little different. This episode was recorded live at our 2026 annual personal wealth conference at the Grove Park Inn in Asheville, North Carolina. Stephan is joined by Deon Strickland, Ph.D. and Derek Cheshire, CFP®, EA for a live Q&A panel, fielding questions submitted on the spot by conference attendees. Topics include the pros and cons of paying cash for a home, annual gift tax exclusion strategies for large families, structuring inheritances for young adults, trust disputes between beneficiaries, troubled real estate syndications, ISO exercises and AMT credits, talking to your kids about money, evaluating a hedge fund, and navigating a parent's estate after a spouse passes.
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Episode 52: Self-Directed IRAs, EU Citizenship, and the K-Shaped Economy - Scholar Big Picture with Dr. Deon Strickland
April 13th, 2026 | 36 mins 10 secs
asset protection, fbar reporting, foreign bank accounts, international planning, k-shaped economy, market timing, portfolio rebalancing, prohibited transactions, real estate investing, self-directed ira, tax planning
Stephan breaks down why splitting a private real estate loan between a Roth IRA and non-qualified funds at different interest rates is a prohibited transaction risk — and what to do instead. Then, a listener with newly obtained EU citizenship wants to know what U.S. tax and reporting obligations come with foreign bank accounts. To close, Dr. Deon Strickland joins for the quarterly Scholar Big Picture conversation on the K-shaped economy, what AI means for labor versus equity returns, and why industrial metals may be worth watching.
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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 49: Delaware Statutory Trusts, Illiquid Business Wealth, and Designing Legacy Homes
March 23rd, 2026 | 29 mins 19 secs
1031 exchanges, business exit strategy, business owner retirement strategy, concentration risk, delaware statutory trusts, illiquid wealth planning, liquidity event, luxury home design, real estate investing, retirement planning, tax planning
In this episode, we explore how to exit appreciated rental real estate without triggering unnecessary taxes, how entrepreneurs can rebalance wealth away from an illiquid business ahead of a future sale, and in our From the Field segment, what truly distinguishes exceptional luxury residences designed to endure across generations.
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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.