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Qualified Small Business Stock (QSBS): The $10 Million Tax-Free Secret with Attorney Christopher Karachale
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In this special episode of The Liquidity Event, BKFi leaders John and AJ interview tax attorney Christopher Karachale about Qualified Small Business Stock (QSBS) - a powerful tax benefit allowing founders to exclude up to $10 million (or more) from capital gains taxes when selling shares. Key Timestamps:
1:50 - What is QSBS? The $10 million exclusion explained 3:16 - History of QSBS: From 1992 to today's 100% exclusion 8:15 - Qualification requirements: Company & shareholder criteria 11:13 - "Qualified trade or business" explained 12:18 - Prohibited business categories 14:14 - Tips for founders to qualify for QSBS 18:30 - LLC conversion strategies for QSBS 20:45 - Fixing past entity mistakes to qualify 22:54 - LLC to C-Corp conversion: FMV basis benefit 26:15 - 1045 rollovers: Strategy for selling before 5 years 29:04 - QSBS stacking: Advanced strategies with trusts 35:38 - Practical advice for early-stage founders Connect with us: Email: [email protected] Leave a voicemail: memo.fm/liquidityevent
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