Displaying items 1-10 of 18 in total of The Scholar Wealth Podcast with the tag "retirement planning".
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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.
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Episode 47: AI Concentration Risk, Concierge Medicine, and Avoiding Trust Disputes
March 9th, 2026 | 34 mins 22 secs
concentration risk, concierge medicine, estate planning, fiduciary litigation, financial independence, healthcare planning, market timing, portfolio rebalancing, retirement planning, tech concentration, trust strategies
In this episode, we discuss how to manage concentrated exposure to AI-driven tech gains without turning rebalancing into market timing, evaluate whether catastrophic coverage paired with concierge medicine is a rational strategy after financial independence, and speak with fiduciary litigator Ellen Morris about what families can do to proactively reduce trust and estate conflicts.
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Episode 43: Lean Family Office Builds, Trump Accounts, and Angel Investing
February 9th, 2026 | 32 mins 8 secs
angel investing, child savings, concentration risk, family business, family office, financial literacy, private equity investment, retirement planning, tax planning
In this episode, we answer two listener questions that highlight common decisions families face as financial structures and options expand. We discuss how to build a family office without overbuilding too early, how new Trump Accounts fit alongside existing child savings options, and close with a From the Field conversation on how angel investors evaluate risk and judgment when outcomes are uncertain.
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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.
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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.