Shows
Insurtechs.ioUnlocking QSBS for Startup Founders with Christopher KarachaleIn this episode, host Jeff Shi welcomes Christopher Karachale, a leading tax attorney and expert on Qualified Small Business Stock (QSBS). They dive deep into what founders, investors, and early employees need to know about QSBS and how it can dramatically reduce tax liability during an exit. Christopher explains the mechanics of QSBS—from original issuance and the $50M gross assets test to the five-year holding requirement—while also clarifying common pitfalls around LLC conversions, S-corp elections, and secondary sales. The discussion highlights how insuretech founders can maximize their eligibility, whether through structuring early, leveraging IP contributions, or using adva...
2025-09-2436 min
Building More Than BusinessThe 2025 QSBS overhaul: New rules, bigger opportunitiesThe qualified small business stock (QSBS) exclusion just got a major upgrade —unlocking even greater tax benefits for eligible shareholders.In this episode of Building More Than Business, our hosts sit down with tax attorney Christopher Karachale to break down what’s changed under the One Big Beautiful Bill Act (OBBBA) and what it means for founders, early employees and investors. They explore key updates to the QSBS rules, including a new $15M gain exclusion cap and tiered holding periods.You’ll also hear how planning strategies like trust stacking, LLC-to-C-corp conversions and Section 1045 rollovers work i...
2025-09-1625 min
The Liquidity Event | Money and Finance with Shane and Ally JaneQualified Small Business Stock (QSBS): The $10 Million Tax-Free Secret with Attorney Christopher KarachaleIn 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...
2025-03-1438 min
2021-09-3016 min