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.

Episode 47: AI Concentration Risk, Concierge Medicine, and Avoiding Trust Disputes

March 9th, 2026  |  34 mins 22 secs

concentration risk, concierge medicine, estate planning, fiduciary litigation, financial independence, healthcare planning, market timing, portfolio rebalancing, retirement planning, tech concentration, trust strategies

In this episode, we discuss how to manage concentrated exposure to AI-driven tech gains without turning rebalancing into market timing, evaluate whether catastrophic coverage paired with concierge medicine is a rational strategy after financial independence, and speak with fiduciary litigator Ellen Morris about what families can do to proactively reduce trust and estate conflicts.

Episode 42: Managing Inherited Property, Protecting Physician Wealth, and Inside the Bourbon Market

February 2nd, 2026  |  42 mins 57 secs

asset protection, bourbon collecting, concentration risk, estate planning, financial literacy, inheritance planning, inherited property, legal exposure, ownership tradeoffs, passion investing, physician finance, real estate investing, tax planning, trust strategies, vacation rental

In this episode, we answer two listener questions that highlight common tradeoffs as wealth and complexity grow. We discuss how to approach inherited real estate when illiquidity and emotional attachment are involved, how high-net-worth physicians can think about asset protection as income and exposure rise together, and close with a From the Field conversation on what actually drives quality and value in the bourbon market.

Episode 37: Qualified Opportunity Zones, IDGTs, and Modern Estate Management

December 29th, 2025  |  38 mins 25 secs

business exit strategy, business sale planning, estate management, estate planning, family business, high-net-worth home management, inheritance planning, intentionally defective grantor trust, liquidity event, qualified opportunity zones, real estate investing, tax planning, trust strategies

Evaluating Qualified Opportunity Zone investments after a large business sale requires balancing tax incentives with risk and liquidity.

IDGTs can help transfer future business growth, but they introduce meaningful cash flow and complexity considerations.

In our From the Field conversation, Peter Hansen explains what modern estate management looks like and how staffing and systems help homes run smoothly.

Episode 35: AI IPO Scenarios, IRA and Roth Timing, and Digital Legacy Preservation

December 15th, 2025  |  26 mins 2 secs

concentration risk, digital legacy planning, estate planning, financial literacy, ipo planning, ira contribution deadlines, iso amt planning, liquidity event, photo and story preservation, roth conversion rules, rsu taxation, stock option exercise, tax planning, trust strategies

This week:
How to approach RSUs, ISOs, and tax planning when your AI startup hints at an IPO.
Why IRA contributions follow one deadline while Roth conversions follow another.
Practical steps for building and preserving a meaningful digital legacy with guest Robyn Sechler.

Episode 31: Bridge Loan Tradeoffs, Private Market 401(k)s, and 1031 Exchange Strategies

November 17th, 2025  |  29 mins 27 secs

estate planning, executive compensation, financial independence, financial literacy, liquidity event, portfolio rebalancing, real estate investing, tax planning, trust strategies

This week, we break down when it makes sense to sell investments versus borrow for a new home, what to know about private market options in 401(k)s, and how 1031 exchanges can reshape long-term real estate planning with guest Julie Baird of First American Exchange Company.

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.

Episode 28: Historic Home Incentives, Valuation Discounts, and the Luxury Yacht Market

October 27th, 2025  |  28 mins 32 secs

construction budgeting, estate planning, estate tax efficiency, family llc planning, family office investing, family wealth transfer, financial independence, financial literacy, gifting strategies, historic property renovation, home restoration costs, independent appraisal, irs valuation scrutiny, lack of marketability discount, luxury asset management, minority interest discount, national register of historic places, preservation incentives, real estate investing, tax credits, tax planning, trust strategies, valuation discounts, virginia historic tax credit, yacht ownership

We discuss restoring historic properties, gifting family LLC interests, and the financial realities of yacht ownership. Topics include federal and state tax credits for historic renovations, how valuation discounts create tax-efficient transfers, and insights from Steve Myers of YATCO on the evolving role of family offices in the global yacht market.

Episode 27: Triple Net Leases, Trust Gifting, and Lessons from SEC Whistleblower Cases

October 20th, 2025  |  39 mins 47 secs

alternative investments, commercial real estate, concentration risk, estate planning, family wealth, fiduciary vs suitability, gifting strategies, income strategy, irrevocable trust, legacy planning, leveraged real estate strategy, lifetime gift exemption, liquidity planning, multigenerational wealth transfer, portfolio diversification, private investment fraud, real estate investing, sec whistleblower, tax planning, triple net lease, trust strategies

This week, Stephan answers two listener questions — how to evaluate triple net lease opportunities with a $5 million budget, and how high-net-worth families should begin transferring wealth to their children through irrevocable trusts. Then, in our From the Field segment, Scott Silver and David Chase share insights from their work as SEC whistleblower attorneys and discuss how investors can protect themselves from fraud in private markets.

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.