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.

Episode 8: Three Physicians, Three Big Questions: Planning for Flexibility, Savings, and Sanity

June 9th, 2025  |  19 mins 24 secs

financial independence, financial literacy, locum tenens retirement accounts, physician burnout, physician finance, retirement planning, variable income planning

Feeling burned out but unsure if you can afford to cut back? We answer physician finance questions about retirement accounts, variable income planning, and what financial independence looks like when you’re ready for a slower pace.

Episode 3: Tax Planning, CPAs, and the Final Stretch to Retirement

May 5th, 2025  |  9 mins 53 secs

cpa coordination, financial readiness, holistic planning, income modeling, liquidity management, portfolio allocation, pre-retirement strategy, retirement planning, roth conversions, sequence of returns risk, tax efficiency, tax planning

What’s the difference between tax planning and tax advice—and when should you involve your CPA?
In this week’s Scholar Wealth Podcast, Stephan Shipe breaks down how financial advisors and accountants work together to optimize tax outcomes, then walks through what it really means to prepare for retirement when you’re just a few years away.

From Roth conversion timing and income modeling to portfolio structure and cash flow strategy, this episode explores how proactive planning today can make your next major financial transition far smoother.

Episode 1: Launching the Scholar Wealth Podcast

April 21st, 2025  |  5 mins 45 secs

asset protection, business exit strategy, charitable giving, concentration risk, corporate cash strategy, deferred compensation, estate planning, executive compensation, family business, family wealth, financial education, financial independence, financial planning, gifting strategies, high net worth, inflation planning, inheritance planning, investment strategy, ipo planning, legacy planning, liquidity event, market timing, philanthropy, physician finance, portfolio rebalancing, private equity investment, real estate investing, retirement planning, stock option exercise, tax planning, trust strategies, vacation rental, wealth management

In our debut episode, host Stephan Shipe shares the story behind the Scholar Wealth Podcast and what listeners can expect each week. Designed for families with complex wealth, the show goes beyond the basics to deliver expert insights, real stories, and practical answers to your most sophisticated financial questions.