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 22: Trusts vs Wills, Senior Living REITs, and a Physician Bonus Playbook

September 15th, 2025  |  22 mins 38 secs

backdoor roth, donor-advised fund considerations, emergency fund strategy, estate complexity, estate planning, fee transparency, financial literacy, inheritance planning, liquidity constraints, manager quality assessment, physician finance, physician taxable account, private reit due diligence, probate avoidance, real estate investing, senior living investment, signing bonus allocation, tax planning, taxable investing, trust strategies, will vs trust

A $5 million estate. A private senior living REIT. A physician’s $75,000 signing bonus. In this Q&A episode, Stephan unpacks three listener questions with clear, practical guidance for high-net-worth families.

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.

Episode 19: Helping Family, Law Firm Partnership Buy-In, and Using NUA: High-Stakes Money Decisions

August 25th, 2025  |  24 mins 1 sec

advisor red flags, asset protection, career transitions, family finance, financial literacy, high-net-worth strategy, partnership buy-in, retirement decisions, retirement planning, tax efficiency, tax planning

Big financial decisions often carry more risk than they first appear. In this episode of the Scholar Wealth Podcast, Stephan answers three listener questions on high-stakes money moves: helping family with a major purchase, evaluating a $500,000 law firm partnership buy-in, and deciding whether to use the Net Unrealized Appreciation (NUA) tax strategy in retirement.

Plus, in our Advisor Red Flags segment, we spotlight why “exclusive” alternative investment opportunities aren’t always as good as they sound.

Episode 16: Big Money Moves: Diversifying, Funding Kids’ Futures, and Buying Abroad 

August 4th, 2025  |  18 mins 52 secs

10b5-1 plan, 529 plan funding, charitable remainder trust, company stock diversification, financial literacy, international property purchase, tax planning

In this episode, we answer listener questions about diversifying concentrated company stock with a 10b5-1 plan, avoiding overfunding 529 plans, and the key considerations before buying a second home abroad. Plus, our Term of the Day breaks down Charitable Remainder Trusts (CRTs) in plain English.

Episode 12: LLCs, Interest Rates, and Rebalancing: Smart Moves in a Shifting Market

July 7th, 2025  |  20 mins 13 secs

federal reserve policy, finance app, interest rates, llc formation, portfolio rebalancing, solo consulting, tax planning

Starting a consulting business? Wondering if an LLC is worth it? In this episode, we tackle entity selection for solo entrepreneurs, how to think through tax treatment, and what structure gives you the best retirement plan options. We also dig into why the Fed hasn’t lowered interest rates yet—and what that means for investors navigating today’s uncertain landscape. Finally, we answer a common question: how often should you rebalance your portfolio in a market like this? Plus, in this week’s Tool Spotlight, we highlight Kubera, a powerful net worth tracking tool for clients with complex assets.

Episode 5: From Startup Exits to Luxury Properties: High-Income Tax Planning and Wealth Strategies for Founders and Medical Pros

May 19th, 2025  |  22 mins 18 secs

charitable fund, charitable giving, luxury property decision, mortgage payoff decision, tax planning

Sold your startup or earning big as a physician? In this episode, we answer questions about high-income tax strategies, smart property investing, and how to prioritize competing financial goals—from retirement to philanthropy.