Displaying items 1-10 of 54 in total of The Scholar Wealth Podcast with the tag "tax planning".
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Episode 78: The 351 Conversion Breakdown, a 400-Acre Farm Legacy Fight, and Patterns After Seven Years
October 12th, 2026 | 25 mins 5 secs
concentration risk, estate equalization, estate planning, family business, family farm estate planning, financial independence, inheritance planning, irs ruling, retirement planning, section 351, tax planning, wealth planning patterns
Stephan takes three listener questions this week. A listener who ran a Section 351 ETF conversion earlier this year to diversify a $4.2 million concentrated position wants to know what the IRS’s new Revenue Ruling 2026-20 means for him. A 400-acre Pennsylvania family farm has three siblings pulling in three directions. And after seven years at Scholar, Stephan adds a handful more patterns to the ones from the Q3 Advisor Desk letter, including the $10 million complexity trap, the retiring-early myth, and why grandkids ruin financial plans.
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Episode 75: Selling Your Business Beyond the Earnout, Family Loans and the IRS, Counterfeit Wine
September 21st, 2026 | 40 mins 43 secs
asset protection, business exit strategy, business sale deal structure, collectibles authentication, family gifting strategies, gifting strategies, inheritance planning, intrafamily loans, liquidity event, tax planning, wine collecting
This week on the Scholar Wealth Podcast, Stephan takes on two listener questions and is joined in From the Field by Maureen Downey, founder of Chai Consulting and one of the foremost independent authorities on counterfeit wine. The first listener is preparing to sell his business and, after hearing our earlier earnout episode, wants to know what else in a deal structure can cost sellers at close. The second is a set of parents hoping to help their son and daughter-in-law buy their first home in an expensive market through a below-market family loan, and wants to understand what the IRS actually allows. Maureen walks through how fake wine ends up in top cellars, why an estimated one in five bottles of fine wine on the secondary market is counterfeit, and how The Chai Method authentication process works.
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Episode 74: Cash Balance Plans for High-Earning Physicians, Building a System for Lumpy Income, and Trust Provisions for Adult Kids
September 14th, 2026 | 17 mins 50 secs
adult children inheritance, cash balance plans, contingency attorney finance, estate planning, financial independence, gifting strategies, incentive trusts, inheritance planning, lumpy income planning, physician finance, retirement planning, tax planning, trust strategies
Stephan tackles three listener questions: whether a high-earning locums anesthesiologist should stack a $200K cash balance plan on top of a maxed solo 401(k), how a contingency attorney with wildly lumpy income and no plans to retire should build a real financial system, and what trust provisions preserve adult kids' drive without controlling from the grave.
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Episode 72: The Uninterested Heir, Earnout Reality Check, and Hiring a Nanny
August 31st, 2026 | 28 mins 42 secs
business exit strategy, business sale earnout planning, financial literacy, gifting strategies, gifting to adult children, household staff, inheritance planning, liquidity event, nanny, tax planning
A self-managed investor asks whether his 28-year-old son should use a wealth manager. A business owner selling on an earnout tries to figure out how much of it to plan around. And Stephanie Fornaro of Hello Nanny on the mistakes families make when they hire household support.
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Episode 70: The Boulder Home Decision, What "Complex" Really Means, and Generational Wealth Stewardship with Lisa McCurdy
August 17th, 2026 | 33 mins 48 secs
charitable giving, concentration risk, estate planning, estate tax exemption, gifting strategies, inheritance planning, legacy and family stewardship, sbloc, tax planning, trust strategies
Stephan works through two listener questions this week. First, a couple weighing three ways to buy a $2.8 million second home in Boulder and disagreeing about whether an SBLOC belongs on the table. Then, a listener with a $35 million net worth concentrated 80 percent in one stock who wants to know why every advisor he meets calls his situation "complex" when it feels pretty simple from where he sits. In From the Field, legacy planning attorney Lisa McCurdy joins to explain why the human side of estate work, not the paperwork, is what determines whether a plan actually holds up across generations.
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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 65: IPO Access, Dynasty Trusts, and Bitcoin Arbitrage Funds
July 13th, 2026 | 26 mins 11 secs
alternative investments, concentration risk, cryptocurrency investing, dynasty trusts, estate planning, financial independence, gifting strategies, inheritance planning, ipo planning, tax planning, trust strategies
Three listener questions this week: a Bay Area tech executive working out how to get real access to IPOs after landing only 13% of his SpaceX allocation, a family pressure testing whether the ongoing costs of an irrevocable dynasty trust actually pencil out for long-horizon private investments, and a listener weighing whether Bitcoin arbitrage funds are as market neutral as they appear on paper.