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 44: Oil Well Concentration Risk, Australian Superannuation, and Learning to Fly

February 16th, 2026  |  27 mins 48 secs

alternative investments, australian superannuation, concentration risk, cross-border tax planning, oil well investing, pilot licensing, private equity investment, tax planning

In this episode, we answer two listener questions that highlight how complexity shows up in both private investments and cross-border planning. We discuss concentration risk in private oil well investments and how to think about projected IRRs and illiquidity within an alternatives allocation, then examine how dual U.S.–Australian families should approach Australian superannuation when retiring in the United States. We close with a From the Field conversation on what pilot licensing actually looks like for busy professionals, from training timelines to the real costs and lifestyle flexibility of aviation.

Episode 43: Lean Family Office Builds, Trump Accounts, and Angel Investing

February 9th, 2026  |  32 mins 8 secs

angel investing, child savings, concentration risk, family business, family office, financial literacy, private equity investment, retirement planning, tax planning

In this episode, we answer two listener questions that highlight common decisions families face as financial structures and options expand. We discuss how to build a family office without overbuilding too early, how new Trump Accounts fit alongside existing child savings options, and close with a From the Field conversation on how angel investors evaluate risk and judgment when outcomes are uncertain.

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 40: Solar Tax Write-Offs, Franchise Investment Decisions, and the Scholar Big Picture

January 19th, 2026  |  38 mins 1 sec

commercial solar investing, concentration risk, financial literacy, franchise investing, inflation planning, investment due diligence, market timing, passive investment myths, private equity investment, real estate investing, tax driven investments, tax planning

In this episode of the Scholar Wealth Podcast, Stephan answers two listener questions focused on evaluating investments that look attractive on paper but require deeper analysis. We start with commercial solar investments and large tax write-offs, then turn to franchising and what investors should consider before committing meaningful capital. The episode closes with the Scholar Big Picture, a quarterly conversation with Dr. Deon Strickland on market behavior, economic uncertainty, and what to watch right now.

Episode 39: 529 Planning in an AI World, Raising Grounded Kids, and Understanding REITs

January 12th, 2026  |  28 mins 51 secs

529 plans, financial literacy, higher education, inheritance planning, lifestyle inflation, raising grounded kids, real estate investing, reits, tax planning

In this episode of the Scholar Wealth Podcast, we start with two listener questions facing many high-income families today. First, we discuss how to think about funding a 529 plan when AI is rapidly changing education, careers, and credentialing, and how to plan for college without overcommitting to a single path. We then turn to a lifestyle question about enjoying financial success while raising kids who stay grounded and understand the value of money. In the second half of the episode, we’re joined by Dr. Stace Sirmans, Professor of Finance at Auburn University, for a clear, academic explanation of how REITs work and how they’re structured.

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.

Holiday Special: Working Asset Tax Rules, Equipment Depreciation, and Employee Benefits Planning

December 22nd, 2025  |  7 mins 56 secs

bonus depreciation rules, business owner tax planning, corporate cash strategy, employee benefits design, family business, financial literacy, retirement planning, section 179 depreciation, tax planning, working asset depreciation

In this episode, three year-end planning questions from a business owner covering the tax treatment of working assets, depreciation of specialized equipment, and long-term employee benefits planning. The conversation explores how business owners should think about asset classification, Section 179 and bonus depreciation, and designing sustainable benefits for a long-tenured workforce.