Displaying items 1-10 of 26 in total of The Scholar Wealth Podcast with the tag "retirement planning".
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Episode 69: Fully Paid Lending, The AI Monte Carlo Trap, and Longevity Medicine with Dr. Nathan Ruch
August 10th, 2026 | 36 mins 26 secs
ai, concentration risk, financial independence, longevity, monte carlo simulation, retirement planning, securities lending, tax planning
A listener asks whether he should enroll in Vanguard's Fully Paid Lending Program on a concentrated stock position. Another listener runs a 70,000-scenario Monte Carlo in Claude that gives him a 92.67 percent success rate on his retirement plan — his wife is not convinced, and Stephan sides with her. Plus, Dr. Nathan Ruch of the Princeton Longevity Center on what proactive longevity medicine looks like when resources are not the constraint.
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Episode 68: Q&A Speed Round with Noah and Evan: $5M Bond Question, Private Credit, Whole Life Pitch, and More
August 3rd, 2026 | 30 mins 30 secs
concentration risk, financial independence, hsa receipts strategy, individual bonds vs bond funds, municipal bonds vs treasuries, portfolio rebalancing, private credit sleeve, private equity investment, retirement planning, tax planning, whole life insurance evaluation
Noah and Evan are back for another speed round, working through seven listener questions on portfolio construction and planning. They cover when individual bonds beat bond index funds at scale, whether to layer QQQ or MAGS on top of a VTI-heavy IRA, how to think about a private credit sleeve, the real math on HSA receipts, rebalancing and asset location across account types, municipal bonds at the top tax bracket, and how to evaluate a whole life sales pitch.
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Episode 67: FIRE at 45 and the Underspending Problem, Public Company Board Seats, and Art in Your Estate
July 27th, 2026 | 49 mins 1 sec
art collections, asset protection, board seats, charitable giving, charitable remainder trusts, estate planning, executive compensation, financial independence, fire, inheritance planning, ipo planning, physician finance, retirement planning, tax planning, trust strategies, family limited partnerships
Retired at 45 with a $200,000 spending plan and can't get above $100,000 — the FIRE underspending problem. What to actually ask before joining the board of a company going public. And attorney Asher Rubinstein on keeping art and collectibles from becoming an estate tax problem, from family limited partnerships to charitable remainder trusts.
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Episode 66: The $800K CPA Gap, Negotiating Away From Unvested RSUs, and Money Masters with Mike
July 20th, 2026 | 34 mins 40 secs
charitable giving, deferred compensation, endowment portfolio, estate planning, executive compensation, financial independence, financial literacy, generational wealth transfer, gifting strategies, high income tax strategy, inheritance planning, retirement planning, retirement transition planning, stock option exercise, tax planning
A high earner realizing his CPA is filing history rather than shaping strategy, a professional weighing a competitor offer with $2.8M in unvested RSUs and deferred comp on the line, and Money Masters with Mike on retiring at 56, building an endowment-style portfolio, and passing it on with intention.
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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.