Episode 50: PE Exit Prep, Offshore Account Reporting, and Protecting Collector Vehicles with Hagerty's Trent Abbott

March 30th, 2026  |  34 mins 50 secs

asset protection, business exit strategy, car insurance, expat tax planning, family business, financial literacy, foreign account compliance, international planning, liquidity event, pe sale preparation, physician finance, private equity investment, specialty asset coverage, tax planning

This week on the Scholar Wealth Podcast, Stephan walks through what a business owner should be doing in the years before entering a formal sale process, using the example of a regional physical therapy group fielding private equity interest. He then addresses the foreign account reporting obligations that can put returning expats out of compliance without realizing it. Finally, Trent Abbott, Vice President of Global Development at Hagerty, joins to discuss how families with significant vehicle collections should think about specialty insurance, agreed value coverage, and the unique risks that standard auto policies miss.

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.

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 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 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 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.