The Scholar Wealth Podcast - Episodes Tagged with “Retirement Planning”

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

Scholar Financial Advising, LLC — Mon, 25 May 2026 05:00:00 -0400

"In this episode, we hear from a business owner in his mid-forties with around ten million saved who has noticed that every financial milestone, hitting his first million, paying off the house, watching the number keep climbing, has failed to bring the sense of arrival he expected. Stephan walks through why the pattern is so common, how the marginal value of every additional dollar changes once basic needs are met, and the mistakes that follow when someone ties their identity to a number rather than to what the wealth actually enables.

Next, we hear from a software engineer at one of the major AI companies heading toward what could be the largest IPO in history, sitting on equity worth more than fifteen million if everything holds. With SpaceX, Anthropic, and OpenAI all approaching potential liquidity events, Stephan explains why the pre-IPO window is where the most planning leverage exists, how ISOs and the alternative minimum tax create real liquidity problems, how the one-and-two-year holding periods unlock long-term capital gains treatment, and where charitable planning through a donor-advised fund can fit in before the event rather than after.

In our From the Field segment, we are joined by Matt Lutz, Managing Director of Flatwater Homes, a luxury residential construction firm based in Milwaukee with more than 40 years of experience delivering some of the most technically extraordinary private builds in North America. We talk about a one-of-a-kind glass-walled natatorium, an underground 30-car garage, the features that push the boundaries of what is possible, and what an ongoing relationship between a family and their builder actually looks like across decades.

Stay in touch beyond the podcast:
Newsletter: https://scholarfinancialadvising.com/newsletter
Start your planning journey: https://scholarfinancialadvising.com/welcome
Submit a question for the show: https://scholarfinancialadvising.com/podcast

Disclaimer: The information provided in this podcast is for general informational and educational purposes only and should not be considered financial, investment, or professional advice. The opinions expressed by the hosts and guests are their own and do not necessarily reflect the views of any affiliated organizations. Investing involves risk, including the potential loss of principal. Past performance is not indicative of future results. Listeners should consult with a qualified financial advisor or professional before making any financial decisions based on the content of this podcast. The hosts and guests are not responsible for any actions taken based on the information shared. Always consider your individual financial situation, objectives, and risk tolerance. Thanks for listening!

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

Scholar Financial Advising, LLC — Mon, 18 May 2026 05:00:00 -0400

This week we're doing something a little different. Instead of the usual two-question format with a guest interview, we're handing the mic over to Associate Financial Advisors Noah Lewis and Evan Mills for a Q&A speed round covering eight shorter questions from listeners.

The first half focuses on investing. Noah and Evan discuss how to think about AI as a structural shift without taking on outsized concentration risk, why international allocation still has a place in a portfolio even after a decade of US outperformance, and whether a retiree should restructure to live off dividends or take a total return approach with strategic selling. They also work through why an intermediate-term bond ETF like BIV might be preferred over a money market fund, and where I-bonds and TIPS fit into the current rate environment.

The second half turns to planning. The conversation covers smarter ways for grandparents to fund private school tuition beyond just writing a check, how the new SECURE 2.0 provision for rolling overfunded 529 balances into a Roth IRA actually works, and the differences between charitable remainder trusts and donor advised funds and when each one makes sense.

Disclaimer: The information provided in this podcast is for general informational and educational purposes only, and is not intended to constitute financial, investment, or other professional advice. The opinions expressed are those of the hosts and guests and do not necessarily reflect the views of any affiliated organizations. Investing in financial markets involves risk, including the potential loss of principal. Past performance is not indicative of future results. Before making any investment decisions, you should consult with a qualified financial advisor who can assess your individual financial situation, objectives, and risk tolerance. Thanks for listening!

Episode 55: 529 Superfunding, Evaluating Memberships After a Liquidity Event, and Concierge Nursing

Scholar Financial Advising, LLC — Mon, 04 May 2026 05:00:00 -0400

When you have a $40 million estate and four grandchildren, superfunding 529s can feel like an obvious estate planning move — but the math isn't always as clean as it looks. Stephan explains how the five-year election works, how it interacts with your annual gifting strategy, and why at this level of wealth, 529s may be the wrong vehicle entirely when compared to trusts, GRATs, or direct giving.

Next, Stephan addresses the very common situation that follows a major exit: everyone wants a piece of it. From an $85,000 golf club initiation to fractional aviation cards to family office intro services, the pitches are relentless and they all sound reasonable. Stephan offers a clear framework for how to evaluate each category — and why the answer for most of them, at least right now, is probably no.

Finally, Jasmine Bhatti of NaviNurses joins to pull back the curtain on what personalized healthcare looks like for families who want more than the standard of care. The conversation covers private duty nursing, how to use long-term care policies strategically before hitting an exclusion threshold, post-surgical recovery at home versus skilled nursing facilities, and the broader concierge healthcare ecosystem — from longevity medicine to integrative physicians to nurses as connectors across the entire care landscape.

Episode 54: Mortgages, Trusts, Hedge Funds, and More: Live Q&A from Our Annual Conference

Scholar Financial Advising, LLC — Mon, 27 Apr 2026 05:00:00 -0400

This episode was recorded live at our 2026 annual personal wealth conference at the Grove Park Inn in Asheville, North Carolina, where about 60 investors, business owners, and successful families gathered for two days of focused conversations on markets, strategy, and long-term wealth planning.
Stephan is joined by Deon Strickland, Ph.D. and Derek Cheshire, CFP®, EA to answer questions submitted on the spot by conference attendees. The result is a wide-ranging conversation covering some of the most pressing questions that come up for families who have built something significant, from the mechanics of mortgages and trusts to the harder conversations around aging parents, inherited money, and teaching the next generation about wealth.

Episode 53: Structured Family Support, Cash Balance Plans, and Hiring a Private Chef

Scholar Financial Advising, LLC — Mon, 20 Apr 2026 05:00:00 -0400

A listener shares that they've given their adult son roughly $180,000 informally over the years and it hasn't solved anything. Stephan walks through how to shift from reactive giving to intentional structure, including savings match programs, conditional support tied to milestones, and when a discretionary trust makes sense.

Then, a consultant asks about layering a cash balance plan on top of a maxed-out solo 401(k). Stephan explains how the two plans interact, what actuarial requirements are involved, and why stable income is the key factor in whether this strategy actually makes sense.

Finally, Chris Demaillet of Montclair Chef joins From the Field to talk about what the private chef placement process looks like for families, from defining what you need to understanding cost structure, personality fit, and what it takes to maintain consistency across multiple residences.

Episode 49: Delaware Statutory Trusts, Illiquid Business Wealth, and Designing Legacy Homes

Scholar Financial Advising, LLC — Mon, 23 Mar 2026 05:00:00 -0400

In this episode, we begin with a listener looking to simplify a real estate portfolio in their early 60s. With multiple properties and significant appreciation, selling outright would trigger both capital gains and depreciation recapture. Stephan walks through how Delaware Statutory Trusts function within a 1031 exchange, the appeal of moving from active management to passive ownership, and the tradeoffs around fees, control, and long-term flexibility. He also reframes the decision more broadly: whether continuing to own real estate still aligns with the family’s overall plan.

Next, we turn to a common but often overlooked issue among entrepreneurs. A listener with $12 million in net worth, largely tied up in a business and real estate, has very little in traditional retirement accounts. Stephan outlines how to begin correcting that imbalance over the decade leading up to a potential exit, including building liquidity through taxable accounts, using high-contribution retirement structures like cash balance plans, and shifting the business from a growth-focused model to one that generates consistent cash flow and commands a higher valuation multiple.

In our From the Field segment, we explore what separates homes that simply look expensive from residences designed to endure. The conversation with Blake Sutton of Est Est Interior Design covers how assembling the right team early can reduce uncertainty in the custom home process, why experienced homeowners approach design decisions differently, and how timeless materials and thoughtful planning contribute to homes that function well across multiple properties and generations.

Stay in touch beyond the podcast:

Newsletter: https://scholarfinancialadvising.com/newsletter

Start your planning journey: https://scholarfinancialadvising.com/welcome

Submit a question for the show: https://scholarfinancialadvising.com/podcast

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

Scholar Financial Advising, LLC — Mon, 09 Mar 2026 05:00:00 -0400

This week, we begin with a listener whose $6 million portfolio has drifted from 25% to 42% in large-cap tech following the AI-driven surge. Stephan reframes the issue as portfolio drift rather than a market call, and walks through how to think about concentration risk, disciplined rebalancing, and tax-aware trimming without reacting to headlines.

Next, we examine healthcare planning after financial independence. A couple in their late 40s with $11 million in investable assets is relying on catastrophic coverage while self-paying for routine care and considering a concierge medical practice. We explore whether this structure represents a rational tradeoff, how to stress-test tail risk exposure, and what healthcare decisions look like over a multi-decade retirement.

Finally, Stephan is joined by Ellen Morris, Chair of Fiduciary Litigation at Cozen O’Connor, for a conversation on how trusts and estate plans unravel in practice. They discuss undue influence, capacity concerns, sibling rivalry, and the practical steps families can take to reduce ambiguity and avoid preventable disputes.

Stay in touch beyond the podcast:

Personal Wealth Conference: https://scholarfinancialadvising.com/conference-2026/

Newsletter: https://scholarfinancialadvising.com/newsletter

Start your planning journey: https://scholarfinancialadvising.com/welcome

Submit a question for the show: https://scholarfinancialadvising.com/podcast

Episode 43: Lean Family Office Builds, Trump Accounts, and Angel Investing

Scholar Financial Advising, LLC — Mon, 09 Feb 2026 05:00:00 -0500

How lean is too lean when building a family office, and when does early flexibility turn into future complexity?

In this episode, we answer a listener question on scaling a family office thoughtfully, including the role of fractional CFOs and CIOs, outsourcing functions like cybersecurity and bookkeeping, and knowing when it makes sense to bring capabilities in-house.

Next, we discuss Trump Accounts, the new 530A accounts launching in 2026, and how they compare to existing options like 529 plans, UGMAs, and parent-held brokerage accounts when saving for children. We explore the tradeoffs between control, flexibility, tax efficiency, and simplicity.

Finally, in our From the Field segment, Stephan is joined by Christian Haller for a conversation on angel investing. They discuss how founders approach investing after an exit, how angel groups evaluate early-stage companies, and the role of judgment, diversification, and patience in building an angel portfolio.

Stay in touch beyond the podcast:

Personal Wealth Conference: https://scholarfinancialadvising.com/conference-2026/
Newsletter: https://scholarfinancialadvising.com/newsletter

Start your planning journey: https://scholarfinancialadvising.com/welcome
Submit a question for the show: https://scholarfinancialadvising.com/podcast

Episode 38: Social Security Timing, Home Sale Capital Gains, and Educational Travel with Road Scholar

Scholar Financial Advising, LLC — Mon, 05 Jan 2026 05:00:00 -0500

In this episode of the Scholar Wealth Podcast, we work through two listener questions that reflect the financial and personal tradeoffs many high earners face as they approach retirement.

We begin with a question about Social Security timing. A high-income listener wonders whether it makes sense to claim benefits early and invest them, rather than waiting until age 70, especially given concerns about potential benefit changes and future means testing. Stephan walks through how Social Security actually works, why delayed benefits function more like longevity insurance than an investment, and how to think realistically about policy risk and guaranteed income.

Next, we turn to a housing question from a long-time homeowner in a high appreciation market. After decades of growth, selling a primary residence can trigger a substantial capital gains tax bill, which often causes families to hesitate even when a move makes sense from a lifestyle perspective. We discuss how the primary residence exclusion works, why six-figure tax bills are common in these situations, and how to evaluate tradeoffs between taxes, flexibility, and family priorities.

In our From the Field segment, we’re joined by Kelsey Perri from Road Scholar. We talk about educational travel in retirement, trends in multi-generational and grandparent travel, and why shared experiences and lifelong learning often become a priority once the financial foundation is in place.

Stay in touch beyond the podcast:

Personal Wealth Conference: https://scholarfinancialadvising.com/conference-2026/
Newsletter: https://scholarfinancialadvising.com/newsletter
Start your planning journey: https://scholarfinancialadvising.com/welcome
Submit a question for the show: https://scholarfinancialadvising.com/podcast

Holiday Special: Working Asset Tax Rules, Equipment Depreciation, and Employee Benefits Planning

Scholar Financial Advising, LLC — Mon, 22 Dec 2025 05:00:00 -0500

In this episode of the Scholar Wealth Podcast, we work through three business planning questions that touch on how assets, equipment, and employees are treated from a tax and benefits perspective.

We start with a question about the tax treatment of working assets. Stephan walks through how the IRS distinguishes between a legitimate business activity and a hobby, why profit motive and documentation matter, and how depreciation rules apply to working animals used in an active trade or business.

Next, we turn to equipment purchases and depreciation. Stephan explains how specialized business equipment is classified, how Section 179 and bonus depreciation work, and why tax benefits should support business decisions rather than drive them.

Finally, we look at employee benefits planning for a long-tenured workforce. Stephan discusses how retirement plans and health benefits should be designed with longevity and sustainability in mind, and why periodic review is critical as workforce demographics and costs evolve.

And if a few of these questions feel a little seasonal, we’ll just say this episode is arriving at the perfect time of year.

Stay in touch beyond the podcast:

Newsletter: https://scholarfinancialadvising.com/newsletter

Start your planning journey: https://scholarfinancialadvising.com/welcome
Submit a question for the show: https://scholarfinancialadvising.com/podcast

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

Scholar Financial Advising, LLC — Mon, 01 Dec 2025 05:00:00 -0500

This week on the Scholar Wealth Podcast, we look at three areas that matter for high-net-worth families. Stephan explains how exchange funds can reduce concentration risk for investors holding large amounts of appreciated stock, including the tradeoffs and IRS rules that determine when these structures make sense. Then we turn to IRMAA — how Medicare’s income-based surcharges are calculated, why the two-year lookback surprises so many new retirees, and what planning strategies can help when income is uneven across years. Finally, Stephan is joined by Perri Dash, founder of Super Niche and co-creator of the Wrist Check Pod, for a conversation on the economics of luxury watches, including brand dynamics, scarcity, spend-history rules, and how collectors think about long-term value.

NEXT STEPS

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Episode 26: Roth Conversions, Gold at Record Highs, and Elite College Admissions

Scholar Financial Advising, LLC — Mon, 13 Oct 2025 05:00:00 -0400

This week, Stephan breaks down what to consider before converting a 401(k) to a Roth — from comparing current and future tax brackets to using partial conversions and asset location to minimize taxes.

Next, he turns to the headlines about gold hitting record highs and explains how investors should think about gold’s role in a portfolio without getting caught up in short-term performance.

And in our From the Field segment, Stephan is joined by Lindsay Tanne Howe, Founder and CEO of LogicPrep https://www.logicprep.com/
a premier college advisory firm that helps students tell their stories and gain admission to top universities. Lindsay shares how families can approach the admissions process strategically, the evolving role of legacy and philanthropy, and why authenticity and early planning matter most.

📅 Upcoming Webinar:
Join Stephan for a deeper discussion on gold and alternative investments — including how these assets fit into a diversified portfolio — on Thursday, November 13.
👉 Register here: https://form.jotform.com/252663253624053?utm_source=podcast

Have a question for a future episode? Submit it at scholaradvising.com/podcast.

Episode 24: Family Gifting Expectations, Tech IPO Decisions, and the Capital Call Dilemma

Scholar Financial Advising, LLC — Mon, 29 Sep 2025 05:00:00 -0400

This week, we take on three listener questions that reveal the real-life complexity of wealth planning.

First, how should parents handle fairness in gifting when one child values a large family wedding and another prefers a smaller celebration but asks for the same amount in cash?

Next, a tech executive with most of his $6 million net worth tied up in stock options faces the uncertainty of an upcoming IPO. We’ll look at how to balance concentration risk, cash flow needs, and long-term upside.

Then, we turn to a capital call in a real estate syndication — should you double down with more money, or accept dilution and walk away?

And in our Myth or Money segment, we challenge the belief that turning 65 means it’s time to shift most of your portfolio out of equities.

Have a question for a future episode? Submit it at scholaradvising.com/podcast.

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

Scholar Financial Advising, LLC — Mon, 25 Aug 2025 05:00:00 -0400

This week’s episode opens with a listener wondering whether to help their brother with a down payment on a new home. The brother plans to repay the funds after selling his current house, but how do you balance protecting your wealth with supporting family? Stephan breaks down the risks, protections, and alternatives to consider.

Next, we hear from an attorney preparing to make partner at their law firm. The expected buy-in is $500,000, and while average partner compensation is significantly higher, the question is: how do you know if the investment is worth it and the best way to finance it?

Finally, a soon-to-retire listener with $3 million in their 401(k) — including $800,000 of company stock — asks whether the Net Unrealized Appreciation (NUA) strategy could reduce their tax bill. We walk through how NUA works, the math behind it, and the risks to watch out for.

And in this week’s Advisor Red Flags, we spotlight so-called “exclusive” investment opportunities that may be more dangerous than desirable.

Have a question for a future episode? Submit it at scholarfinancialadvising.com/podcast.

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

Scholar Financial Advising, LLC — Mon, 18 Aug 2025 05:00:00 -0400

In this episode of the Scholar Wealth Podcast, we tackle big wealth strategy questions. First, Stephan answers whether now is the right time to sell a gold coin collection worth $250,000, with gold prices at record highs. We cover how to value a gold collection, when to sell gold coins, and how to identify a fair auction house commission versus being taken advantage of.

Next, we explore currency diversification for high-net-worth investors, including whether moving several million into foreign currencies or international bonds is a smart hedge against US dollar risk and banking system instability. Stephan shares the pros and cons of international bond funds, currency hedging strategies, and proportional allocations for large portfolios.

Finally, in our Money Masters segment, special guest Byron shares his journey as a successful DIY investor—how he built confidence in managing his own investments, reached financial independence, and reinvented himself in retirement. It’s a conversation about second-act planning, wealth protection, and making work optional.

Disclosures: The guest on this podcast was a client of Scholar Financial Advising as of the date of recording, and was not compensated for their time. Nothing conveyed by the guest should be construed as a testimonial or endorsement of Scholar Financial Advising, and their experience as an investor or a client may not be representative of all investor or client experiences. The information provided in this podcast is for general informational and educational purposes only, and is not intended to constitute financial, investment, or other professional advice, the opinions. expressed are those of the hosts and guests and do not necessarily reflect the views of any affiliated organizations. Investing in financial markets involves risk, including the potential loss of principle, past performance is not indicative of future results. Before making any investment decisions, you should consult with a qualified financial advisor, who can assess your individual financial situation, objectives and risk tolerance.

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

Scholar Financial Advising, LLC — Mon, 09 Jun 2025 05:00:00 -0400

Three physicians. Three very different financial questions. In this episode, we unpack real scenarios from high-income earners navigating career growth, variable income, and burnout.

First, we address retirement planning for locum tenens physicians—what options exist when there’s no employer-sponsored plan?

Next, we talk strategy with a private practice physician whose income varies with revenue share.

Finally, we hear from a physician feeling the effects of burnout. With significant assets already saved, she’s asking a question many mid-career professionals face: Can I afford to slow down? We explore how to balance lifestyle changes with long-term financial independence.

In this week’s special segment “Advisor Red Flags," we challenge the common advice that “maxing out your 401(k) is enough."

_Have a question you’d like us to tackle in a future episode? Email us at podcast@scholarfinancialadvising.com
_

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

Scholar Financial Advising, LLC — Mon, 05 May 2025 06:00:00 -0400

In this episode of the Scholar Wealth Podcast, Stephan Shipe explains the crucial difference between tax planning and tax advice—and how collaboration between your financial advisor and CPA can prevent costly surprises. He outlines when to bring your accountant into the process, how proactive modeling can help hedge against future tax increases, and why complex events like IPOs, business sales, and inheritances require coordinated planning.

Stephan then turns to the retirement transition, describing why the five years before and after your target date are the most critical for financial decision-making. He covers how to prepare for income changes, sequence-of-returns risk, and liquidity needs, and why stress testing your plan is essential before leaving the workforce.

Disclaimer: The information provided in this podcast is for general informational and educational purposes only, and is not intended to constitute financial, investment, or other professional advice. The opinions expressed are those of the hosts and guests and do not necessarily reflect the views of any affiliated organizations. Investing in financial markets involves risk, including the potential loss of principal. Past performance is not indicative of future results. Before making any investment decisions, you should consult with a qualified financial advisor, who can assess your individual financial situation, objectives and risk tolerance. Thanks for listening!

Episode 1: Launching the Scholar Wealth Podcast

Scholar Financial Advising, LLC — Mon, 21 Apr 2025 07:00:00 -0400

In this first episode of the Scholar Wealth Podcast, host Stephan Shipe introduces himself, shares the story behind the show, and outlines what listeners can expect each week. With a PhD in finance, years of academic research, and experience advising high-net-worth families, Stephan explains why this podcast was created: to provide clear, expert insights for families facing complex wealth challenges.

From multi-generational legacy planning to executive compensation, business exits, philanthropy, and beyond, this podcast is built for those who want to go deeper than the basics. Stephan also introduces the Scholar Wealth Network, a community designed to connect families with resources, education, and expert perspectives.

Tune in to hear the mission behind the podcast and how you can get involved by submitting your own questions and joining the conversation.

The information provided in this podcast is for general informational and educational purposes only, and is not intended to constitute financial, investment, or other professional advice, the opinions. expressed are those of the hosts and guests and do not necessarily reflect the views of any affiliated organizations. Investing in financial markets involves risk, including the potential loss of principle, past performance is not indicative of future results. Before making any investment decisions, you should consult with a qualified financial advisor, who can assess your individual financial situation, objectives and risk tolerance.