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, 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 33: Exchange Funds, IRMAA Surprises, and the Modern Watch Market

December 1st, 2025  |  37 mins 17 secs

collectible timepieces, concentrated stock, concentration risk, diversification strategies, exchange funds, financial literacy, income smoothing, irmaa, magi, medicare premiums, retirement planning, tax planning, watch market, watch valuation

In this episode,we break down how exchange funds help investors manage concentrated stock positions, explains how IRMAA surcharges work when income fluctuates, and talks with Perri Dash about what truly drives value in the modern luxury watch 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 26: Roth Conversions, Gold at Record Highs, and Elite College Admissions

October 13th, 2025  |  25 mins 20 secs

401k strategy, alternative investments, college admissions, concentration risk, diversification, education planning, estate planning, financial independence, financial literacy, gifting strategies, gold investing, inflation planning, legacy planning, market timing, retirement planning, roth conversion, tax planning, wealth preservation

This episode tackles wealth decisions across two generations: when it makes sense to convert a 401(k) to a Roth, how to think about gold at record highs, and what high-net-worth families should know about navigating elite college admissions with Lindsay Tanne Howe of LogicPrep.

Episode 25: When Spouses Disagree on Legacy Goals, Family Business Concentration Risk, and IRS Audit Insights

October 6th, 2025  |  37 mins 1 sec

concentration risk, estate planning, family business, family company, family dynamics, gifting strategies, inheritance planning, irs audits, legacy disagreements, private business risk, tax planning

This episode tackles family and financial crossroads: how couples can resolve different visions for their legacy, the risks of tying too much wealth to a relative’s business, and expert strategies for handling IRS audits with David De Jong.

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.

Episode 21: All in One Bank, Deferred Comp Timing, and a $20-to-Success Journey

September 8th, 2025  |  36 mins 43 secs

asset protection, company solvency risk, compounding interest, concentration risk, deferred compensation, executive compensation, fdic insurance, financial independence, financial literacy, lump sum vs installment payments, sipc insurance, tax bracket management, tax planning

Two practical questions for high-net-worth families: 1) Is keeping all your cash and investments at one institution a smart simplifier or a hidden risk? We unpack FDIC vs. SIPC, custodial risk, and why splitting liquidity across banks and custodians can protect access. 2) How to choose a deferred compensation distribution schedule when the future is uncertain. We walk through the tradeoffs among company solvency, tax brackets, and your real cash needs. Plus, a Money Masters story who arrived in the US with $20 and built wealth through discipline, compounding, and clear values he now passes to his kids.

Episode 20: Learning Capital for Kids, Tax Loss Harvesting with Direct Indexing, and Hiring a Private Chef

September 1st, 2025  |  22 mins 44 secs

charitable giving, concentration risk, crypto investing, dafs, direct indexing, estate planning, financial independence, financial literacy, gifting strategies, inheritance planning, learning capital, market timing, portfolio rebalancing, qsbs, tax planning, trust strategies

In this episode, we answer listener questions about setting boundaries around “learning capital” when a child wants to invest trust assets in crypto, weighing the benefits of direct indexing for tax loss harvesting in a $6 million taxable portfolio, and handling the financial logistics of hiring a private chef for a family-owned summer residence. Plus, our Term of the Day segment breaks down QSBS — Qualified Small Business Stock — and why it can be such a powerful tax planning opportunity for entrepreneurs.