Displaying all 4 Episode of The Scholar Wealth Podcast with the tag “ipo planning”.
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Episode 35: AI IPO Scenarios, IRA and Roth Timing, and Digital Legacy Preservation
December 15th, 2025 | 26 mins 2 secs
concentration risk, digital legacy planning, estate planning, financial literacy, ipo planning, ira contribution deadlines, iso amt planning, liquidity event, photo and story preservation, roth conversion rules, rsu taxation, stock option exercise, tax planning, trust strategies
This week:
How to approach RSUs, ISOs, and tax planning when your AI startup hints at an IPO.
Why IRA contributions follow one deadline while Roth conversions follow another.
Practical steps for building and preserving a meaningful digital legacy with guest Robyn Sechler. -
Episode 24: Family Gifting Expectations, Tech IPO Decisions, and the Capital Call Dilemma
September 29th, 2025 | 22 mins 20 secs
10b5-1 trading plan, adult children financial expectations, capital call dilemma, concentrated stock risk, concentration risk, de-risking at 65, equity allocation in retirement, experience vs cash gifts, family gifting dynamics, financial literacy, gifting strategies, investment dilution, ipo planning, ipo stock concentration, liquidity event, longevity and investing, mortgage and private school planning, multigenerational wealth communication, private deal due diligence, real estate investing, real estate syndication risks, retirement planning, retirement portfolio strategy, rsu liquidity planning, stock option exercise, wedding gift fairness
This episode tackles three wealth questions you won’t find in a textbook. We discuss how families can approach fairness in gifting when children make very different choices around major life events, how tech executives should think about concentration risk and cash flow ahead of an IPO, and what to do when a real estate syndication deal issues a capital call. Plus, in Myth or Money, we ask whether turning 65 really means it’s time to cut back on equities.
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Episode 11: Estate Planning in Motion: Trust Strategies, IPO Tax Prep, and Smarter Umbrella Insurance
June 30th, 2025 | 23 mins 3 secs
estate planning, estate tax sunset, family limited partnership, ipo planning, ipo tax planning, irrevocable trust, trust strategies, umbrella insurance
This week, we’re answering client questions about big-picture estate planning, preparing for future tax exposure, and protecting family wealth. We’ll cover trust strategies ahead of the 2026 estate tax sunset, key tax considerations for pre-IPO stockholders, and what to expect when shopping for umbrella insurance coverage.
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Episode 1: Launching the Scholar Wealth Podcast
April 21st, 2025 | 5 mins 45 secs
asset protection, business exit strategy, charitable giving, concentration risk, corporate cash strategy, deferred compensation, estate planning, executive compensation, family business, family wealth, financial education, financial independence, financial planning, gifting strategies, high net worth, inflation planning, inheritance planning, investment strategy, ipo planning, legacy planning, liquidity event, market timing, philanthropy, physician finance, portfolio rebalancing, private equity investment, real estate investing, retirement planning, stock option exercise, tax planning, trust strategies, vacation rental, wealth management
In our debut episode, host Stephan Shipe shares the story behind the Scholar Wealth Podcast and what listeners can expect each week. Designed for families with complex wealth, the show goes beyond the basics to deliver expert insights, real stories, and practical answers to your most sophisticated financial questions.