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.

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.

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.

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 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 13: Equity, Exit Plans, and Expensive Zip Codes: Wealth Strategy in Real Life

July 14th, 2025  |  22 mins 28 secs

business exit strategy, estate equalization, gifting down payments, gifting strategies, vacation rental, vacation rental investing

Is it still worth buying a vacation rental? What’s the best way to gift down payments to kids in wildly different housing markets? And how do you start preparing—personally—for a business sale that’s still a few years out? In this episode, we tackle three listener questions around real estate, family gifting strategy, and long-term exit planning. Plus, in this week’s Money in the Headlines, we explore whether wealth really leads to longer life.

Episode 9: Beyond the Paycheck: Vacation Rental ROI, State Taxes, and Deferred Comp Decisions

June 16th, 2025  |  18 mins 43 secs

deferred compensation, financial literacy, no-income-tax state move, residency rules, vacation rental, vacation rental roi

This week, we’re digging into real-world financial decisions with long-term impact. What’s the right way to measure ROI on a vacation rental—and how do you account for taxes, maintenance, and future resale? Thinking of relocating to a no-income-tax state? We explain what to evaluate beyond just taxes, including legal residency rules and estate implications. If you’ve been offered deferred compensation, we’ll walk through how to weigh the benefits, risks, and coordination with other retirement strategies.

Then in Money in the Headlines, Stephan reacts to a new survey showing 77% of Americans are changing their financial behavior due to recession fears. Is that smart strategy—or emotional overreaction?

Episode 1: Launching the Scholar Wealth Podcast

April 21st, 2025  |  5 mins 45 secs

asset protection, business exit strategy, charitable giving, concentration risk, corporate cash strategy, deferred compensation, estate planning, executive compensation, family business, family wealth, financial education, financial independence, financial planning, gifting strategies, high net worth, inflation planning, inheritance planning, investment strategy, ipo planning, legacy planning, liquidity event, market timing, philanthropy, physician finance, portfolio rebalancing, private equity investment, real estate investing, retirement planning, stock option exercise, tax planning, trust strategies, vacation rental, wealth management

In our debut episode, host Stephan Shipe shares the story behind the Scholar Wealth Podcast and what listeners can expect each week. Designed for families with complex wealth, the show goes beyond the basics to deliver expert insights, real stories, and practical answers to your most sophisticated financial questions.