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 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 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.

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.

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 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 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 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 18: When to Sell, When to Hedge, and When to Start Your Second Act

August 18th, 2025  |  27 mins 32 secs

asset protection, auction commissions, currency diversification, financial independence, financial literacy, foreign currency investing, gold investing, inheritance planning, international bond funds, market timing, retirement planning, second act retirement, selling collectibles, wealth premiums

In this episode, we answer a listener question about selling a $250,000 gold coin collection. Then, we explore whether shifting several million dollars into foreign currencies is a smart hedge against instability in the US banking system. Finally, in our Money Masters segment, Byron shares how he built confidence as a DIY investor, achieved financial independence, and reinvented himself in retirement.