Mar 14, 2025
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: liquidityevent@brooklynfi.com Leave a
voicemail: memo.fm/liquidityevent
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