Displaying 2 items of The Scholar Wealth Podcast with the tag "tax loss harvesting".
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Episode 41: Choosing Charitable Impact, Wash Sale Rules, and Business Valuation in Practice
January 26th, 2026 | 38 mins 36 secs
business exit strategy, business valuation, charitable giving, charitable impact, estate planning, family business, nonprofit evaluation, portfolio rebalancing, tax loss harvesting, tax planning, wash sale rules
In this episode, we explore how financial decisions can still feel complicated even when the numbers clearly work. The conversation covers how to choose impactful charitable giving without an existing connection, how wash sale rules show up in real-world portfolios, and a practical discussion with Mike Blake on how business valuations actually work in practice.
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Episode 20: Learning Capital for Kids, Tax Loss Harvesting with Direct Indexing, and Hiring a Private Chef
September 1st, 2025 | 22 mins 44 secs
charitable giving, concentration risk, crypto investing, dafs, direct indexing, estate planning, financial independence, financial literacy, gifting strategies, inheritance planning, learning capital, market timing, portfolio rebalancing, qsbs, tax loss harvesting, tax planning, trust strategies
In this episode, we answer listener questions about setting boundaries around “learning capital” when a child wants to invest trust assets in crypto, weighing the benefits of direct indexing for tax loss harvesting in a $6 million taxable portfolio, and handling the financial logistics of hiring a private chef for a family-owned summer residence. Plus, our Term of the Day segment breaks down QSBS — Qualified Small Business Stock — and why it can be such a powerful tax planning opportunity for entrepreneurs.