Episode 58: The $10M Restlessness, AI IPO Stock Decisions, and Heirloom Construction

May 25th, 2026  |  37 mins 52 secs

charitable giving, concentrated stock, concentration risk, executive compensation, financial independence, ipo planning, iso tax planning, liquidity event, luxury residential construction, pre-ipo planning, retirement planning, stock option exercise, tax planning

A business owner in his mid-forties with ten million saved asks why every financial milestone has failed to feel like arrival, and what mistakes people in his position tend to make. Then a software engineer at one of the major AI companies heading toward a historic IPO asks how to plan around fifteen million in pre-IPO equity, including ISOs, AMT exposure, and the holding periods that unlock long-term capital gains. In From the Field, we are joined by Matt Lutz, Managing Director of Flatwater Homes, for a conversation about luxury residential construction, from underground garages to glass-walled natatoriums.

Episode 57: Q&A Speed Round with Noah and Evan: AI Investing, Living Off Dividends, 529-to-Roth, and More

May 18th, 2026  |  25 mins 28 secs

bond investing, charitable giving, concentration risk, education funding, estate planning, gifting strategies, inflation planning, international planning, investment strategy, retirement planning, tax planning, trust strategies

A Q&A speed round with Associate Financial Advisors Noah Lewis and Evan Mills, tackling eight listener questions across investing and planning. Topics include AI as a structural shift, international allocation, dividends versus selling shares, gifting tuition to grandkids, BIV versus money markets, I-bonds and TIPS, the 529-to-Roth rollover under SECURE 2.0, and charitable remainder trusts versus donor advised funds.

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 47: AI Concentration Risk, Concierge Medicine, and Avoiding Trust Disputes

March 9th, 2026  |  34 mins 22 secs

concentration risk, concierge medicine, estate planning, fiduciary litigation, financial independence, healthcare planning, market timing, portfolio rebalancing, retirement planning, tech concentration, trust strategies

In this episode, we discuss how to manage concentrated exposure to AI-driven tech gains without turning rebalancing into market timing, evaluate whether catastrophic coverage paired with concierge medicine is a rational strategy after financial independence, and speak with fiduciary litigator Ellen Morris about what families can do to proactively reduce trust and estate conflicts.

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, international 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 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 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, 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.