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 46: Evaluating PPLI, Investing in a Child’s Startup, and Cross-Border Tax Complexity

March 2nd, 2026  |  37 mins 32 secs

advanced tax strategies, complex wealth structures, cross-border planning, estate planning, family business, family capital decisions, international planning, private equity investment, tax planning, venture investing

In this episode, we examine three sophisticated planning decisions that sit at the intersection of tax efficiency, family dynamics, and global mobility. We break down how affluent families should evaluate Private Placement Life Insurance beyond the marketing pitch, how to thoughtfully approach investing in a child’s venture-backed startup without distorting incentives or relationships, and close with a From the Field conversation on the real tax and structural complexities of building a life across borders.

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 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.

Episode 38: Social Security Timing, Home Sale Capital Gains, and Educational Travel with Road Scholar

January 5th, 2026  |  31 mins 12 secs

capital gains tax, estate planning, financial independence, inflation planning, inheritance planning, longevity planning, multigenerational travel planning, primary residence sale, real estate investing, retirement planning, social security timing, tax planning

In this episode, we answer two listener questions that highlight common retirement planning tradeoffs. We discuss Social Security timing for high earners, capital gains considerations when selling a long-held primary residence, and how families think about prioritizing meaningful experiences through educational travel with Road Scholar.

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 34: Buying a €450K Home Abroad, Planning Around Carried Interest, and Building a Wine Collection That Lasts

December 8th, 2025  |  34 mins 34 secs

carried interest, concentration risk, cross-border real estate, deferred compensation, estate planning, inheritance planning, international planning, legacy assets, private equity compensation, private equity investment, real estate investing, tax planning, vacation rental, wine collecting

Buying a €450K family home in Portugal often involves emotion, complex tax rules, and long-term management considerations.

Carried interest can be valuable, but payouts are uncertain. Planning should assume a base case of no carry and treat future distributions as upside.

Wine expert Walker Strangis explains how families can build and maintain collections with both personal meaning and financial value.

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.