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, 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, 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.

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 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 26: Roth Conversions, Gold at Record Highs, and Elite College Admissions

October 13th, 2025  |  25 mins 20 secs

401k strategy, alternative investments, college admissions, concentration risk, diversification, education planning, estate planning, financial independence, financial literacy, gifting strategies, gold investing, inflation planning, legacy planning, market timing, retirement planning, roth conversion, tax planning, wealth preservation

This episode tackles wealth decisions across two generations: when it makes sense to convert a 401(k) to a Roth, how to think about gold at record highs, and what high-net-worth families should know about navigating elite college admissions with Lindsay Tanne Howe of LogicPrep.

Episode 25: When Spouses Disagree on Legacy Goals, Family Business Concentration Risk, and IRS Audit Insights

October 6th, 2025  |  37 mins 1 sec

concentration risk, estate planning, family business, family company, family dynamics, gifting strategies, inheritance planning, irs audits, legacy disagreements, private business risk, tax planning

This episode tackles family and financial crossroads: how couples can resolve different visions for their legacy, the risks of tying too much wealth to a relative’s business, and expert strategies for handling IRS audits with David De Jong.