Displaying items 1-10 of 22 in total of The Scholar Wealth Podcast with the tag "retirement planning".
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Episode 64: Gifting at 88, Deferred Comp Defaults, and 100-Year Families
July 6th, 2026 | 40 mins 31 secs
100-year family enterprises, deferred comp elections, deferred compensation, estate planning, executive compensation, family business, financial literacy, gifting strategies, inheritance planning, lifetime gifting to grandchildren, retirement planning, step-up in basis, tax planning, three-generation myth
An 88-year-old mother with $6 million in a brokerage account of embedded gains wants to gift to her grandchildren now, and Stephan works through the tradeoff between lifetime gifting and the step-up at death, the tools that solve the problem without sacrificing basis, and why the honest answer at 88 is rarely more complicated than annual exclusions and direct payments. Then a 51-year-old executive defaulting to lump-sum-at-separation on his deferred comp elections gets a full walkthrough of what's actually at stake — Section 409A irrevocability, credit risk, the tax cliff at separation, and how installment options and in-service distributions coordinate with the years ahead. In From the Field, organizational psychologist Dennis Jaffe joins the show to share what he learned from interviewing 100 families across 22 countries that have thrived past their third generation, why the "three-generation curse" is largely a myth, and how successful families evolve from a single entrepreneur into a cooperative community across generations.
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Episode 63: Partner Buyouts, the Surgeon's Retirement Cliff, and Executive Protection
June 29th, 2026 | 31 mins 4 secs
asset protection, business exit strategy, business valuation, estate planning, executive compensation, executive protection, income cliff planning, partnership buyout, physician finance, retirement planning, surgeon retirement
A founder with an $18M medical staffing business wants to buy out his 22% minority partner before selling in five to seven years, an orthopedic surgeon at 58 plans a retirement around a hard physical expiration date on his hands, and Brendan Weed of Arux Group walks through what personal security and executive protection actually look like for families with significant wealth and visibility.
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Episode 62: The SpaceX IPO, the Magnificent Ten, and What's Quietly Breaking Underneath the Market
June 22nd, 2026 | 36 mins 14 secs
ai investing, concentration risk, financial independence, inflation planning, ipo, magnificent ten, market concentration, market timing, portfolio diversification, portfolio rebalancing, retirement planning, tax planning
Deon Strickland joins Stephan for a quarterly Scholar Big Picture conversation on what the SpaceX IPO says about how investors are pricing AI, the growing concentration risk as the Magnificent Ten approaches forty percent of the S&P 500, and the strange disconnect between a strong stock market and rising credit card defaults. They also work through the case for gold and bonds as shock absorbers, the political path toward higher tax rates and wealth taxes, and what Deon is watching from the new Fed chair and the next inflation print.
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Episode 61: Preparing the Spouse Who Doesn't Manage the Money, When Vacation Rental Income Disappears, and Preparing Heirs with Jessica McGawley
June 15th, 2026 | 29 mins 9 secs
asset protection, estate planning, family business, family governance, family wealth transfer, financial literacy, gifting strategies, inheritance planning, real estate investing, retirement planning, spousal financial planning, trust strategies, vacation rental
A wife who has managed every dollar of her family's $19 million for thirty years faces the reality that her husband doesn't know where any of it is. A couple at 63 lose their beach house rental income overnight when a zoning change kills VRBO on their street. And in From the Field, Jessica McGawley of Dallington joins us on preparing the next generation for wealth, not just preparing the wealth for them.
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Episode 58: The $10M Restlessness, AI IPO Stock Decisions, and Heirloom Construction
May 25th, 2026 | 37 mins 52 secs
charitable giving, concentrated stock, concentration risk, executive compensation, financial independence, ipo planning, iso tax planning, liquidity event, luxury residential construction, pre-ipo planning, retirement planning, stock option exercise, tax planning
A business owner in his mid-forties with ten million saved asks why every financial milestone has failed to feel like arrival, and what mistakes people in his position tend to make. Then a software engineer at one of the major AI companies heading toward a historic IPO asks how to plan around fifteen million in pre-IPO equity, including ISOs, AMT exposure, and the holding periods that unlock long-term capital gains. In From the Field, we are joined by Matt Lutz, Managing Director of Flatwater Homes, for a conversation about luxury residential construction, from underground garages to glass-walled natatoriums.
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Episode 57: Q&A Speed Round with Noah and Evan: AI Investing, Living Off Dividends, 529-to-Roth, and More
May 18th, 2026 | 25 mins 28 secs
bond investing, charitable giving, concentration risk, education funding, estate planning, gifting strategies, inflation planning, international planning, investment strategy, retirement planning, tax planning, trust strategies
A Q&A speed round with Associate Financial Advisors Noah Lewis and Evan Mills, tackling eight listener questions across investing and planning. Topics include AI as a structural shift, international allocation, dividends versus selling shares, gifting tuition to grandkids, BIV versus money markets, I-bonds and TIPS, the 529-to-Roth rollover under SECURE 2.0, and charitable remainder trusts versus donor advised funds.
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Episode 55: 529 Superfunding, Evaluating Memberships After a Liquidity Event, and Concierge Nursing
May 4th, 2026 | 30 mins 28 secs
529 planning, concierge healthcare, estate planning, financial independence, financial literacy, gifting strategies, liquidity event, private club memberships, retirement planning
This week on the Scholar Wealth Podcast, Stephan walks through how 529 superfunding works, how it interacts with an existing annual gifting strategy, and whether it's actually the right estate planning tool for a family with a $40 million estate. He then breaks down a framework for evaluating the flood of pitches that follow a liquidity event — golf clubs, city clubs, private aviation cards, and family office intro services — and how to separate what's genuinely worth it from what just sounds like it should be. Finally, Jasmine Bhatti, founder and CEO of NaviNurses, joins to discuss the personalized healthcare landscape: from private duty nursing and post-surgical recovery care to concierge medicine, longevity practitioners, and integrative health.
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Episode 54: Mortgages, Trusts, Hedge Funds, and More: Live Q&A from Our Annual Conference
April 27th, 2026 | 35 mins 10 secs
estate planning, financial literacy, gifting strategies, incentive stock options, inheritance planning, live q&a, real estate investing, real estate syndication, retirement planning, stock option exercise, talking to kids about money, tax planning, trust distribution, trust strategies
This week, we're bringing you something a little different. This episode was recorded live at our 2026 annual personal wealth conference at the Grove Park Inn in Asheville, North Carolina. Stephan is joined by Deon Strickland, Ph.D. and Derek Cheshire, CFP®, EA for a live Q&A panel, fielding questions submitted on the spot by conference attendees. Topics include the pros and cons of paying cash for a home, annual gift tax exclusion strategies for large families, structuring inheritances for young adults, trust disputes between beneficiaries, troubled real estate syndications, ISO exercises and AMT credits, talking to your kids about money, evaluating a hedge fund, and navigating a parent's estate after a spouse passes.
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Episode 53: Structured Family Support, Cash Balance Plans, and Hiring a Private Chef
April 20th, 2026 | 31 mins 52 secs
adult child financial support, asset protection, business exit strategy, cash balance plan, charitable giving, defined benefit plan, domestic staff hiring, estate planning, family business, family gifting strategy, financial independence, gifting strategies, inheritance planning, private chef placement, retirement contribution stacking, retirement planning, solo 401k, tax planning
A listener asks how to structure financial support for an adult child in a way that builds accountability rather than dependence. Then, a consultant explores whether layering a cash balance plan on top of a solo 401(k) makes sense, and what the long-term funding commitment actually looks like. Chris Demaillet, founder of Montclair Chef, joins From the Field to discuss what families need to know before hiring a private chef.
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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.