In 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 advanced strategies like trust stacking. This episode is a must-listen for startup founders, venture-backed entrepreneurs, and insuretech leaders looking to optimize their tax outcomes at exit.

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Jeff Shi :

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Christopher A. Karachale :

https://www.linkedin.com/in/christopher-karachale-093b1049/

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