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.

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 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 29: CRUT Strategies, Contingency Fee Windfalls, and Protecting Valuable Collections

November 3rd, 2025  |  29 mins 31 secs

art insurance, asset protection, charitable giving, charitable remainder trusts, contingency attorneys, cruts, donor-advised funds, financial literacy, fine art protection, legal windfalls, liquidity event, liquidity management, real estate investing, real estate sales, risk management, tax planning, trust strategies, uneven income planning, valuable collections

This episode examines three sides of wealth protection: how to use a charitable remainder unitrust (CRUT) when selling appreciated real estate, how contingency attorneys should plan after a major payout, and how to safeguard valuable art and collectibles with Anne Rappa of Marsh McLennan Agency.

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 24: Family Gifting Expectations, Tech IPO Decisions, and the Capital Call Dilemma

September 29th, 2025  |  22 mins 20 secs

10b5-1 trading plan, adult children financial expectations, capital call dilemma, concentrated stock risk, concentration risk, de-risking at 65, equity allocation in retirement, experience vs cash gifts, family gifting dynamics, financial literacy, gifting strategies, investment dilution, ipo planning, ipo stock concentration, liquidity event, longevity and investing, mortgage and private school planning, multigenerational wealth communication, private deal due diligence, real estate investing, real estate syndication risks, retirement planning, retirement portfolio strategy, rsu liquidity planning, stock option exercise, wedding gift fairness

This episode tackles three wealth questions you won’t find in a textbook. We discuss how families can approach fairness in gifting when children make very different choices around major life events, how tech executives should think about concentration risk and cash flow ahead of an IPO, and what to do when a real estate syndication deal issues a capital call. Plus, in Myth or Money, we ask whether turning 65 really means it’s time to cut back on equities.